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Chemical Structure| 26608-06-0 Chemical Structure| 26608-06-0

Structure of 26608-06-0

Chemical Structure| 26608-06-0

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CAS No.: 26608-06-0

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Product Details of [ 26608-06-0 ]

CAS No. :26608-06-0
Formula : C12H7BrO
M.W : 247.09
SMILES Code : BrC1=CC=C2C(OC3=CC=CC=C23)=C1
MDL No. :MFCD09966042
InChI Key :AZFABGHLDGJASW-UHFFFAOYSA-N
Pubchem ID :296861

Safety of [ 26608-06-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 26608-06-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 13
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 61.42
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

13.14 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.72
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.81
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.35
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.5
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.9

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.09
Solubility 0.00201 mg/ml ; 0.00000814 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.82
Solubility 0.00375 mg/ml ; 0.0000152 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-5.82
Solubility 0.000374 mg/ml ; 0.00000151 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.39 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.76

Application In Synthesis of [ 26608-06-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 26608-06-0 ]

[ 26608-06-0 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 109-72-8 ]
  • [ 26608-06-0 ]
  • [ 60-29-7 ]
  • [ 71-43-2 ]
  • [ 29021-91-8 ]
  • [ 2786-05-2 ]
  • 2
  • [ 26608-06-0 ]
  • [ 20279-16-7 ]
  • 3
  • [ 26608-06-0 ]
  • [ 67019-91-4 ]
  • [ 65489-80-7 ]
  • 4
  • [ 26608-06-0 ]
  • [ 29021-91-8 ]
  • 6
  • [ 26608-06-0 ]
  • [ 25074-60-6 ]
  • 7
  • [ 26608-06-0 ]
  • [ 4499-66-5 ]
  • 8
  • [ 26608-06-0 ]
  • dibenzofuran-3-yl-triphenyl-plumbane [ No CAS ]
  • 9
  • [ 4106-66-5 ]
  • [ 26608-06-0 ]
YieldReaction ConditionsOperation in experiment
68% To a 500 mL four-necked round bottom flask equipped with a stirrer, a Liebig condenser (not required), a thermometer, and a 200 mL dropping funnel, 19.0 g (102.6 mmol) of the amino compound obtained in the above ,190 mL of water and 57 mL of 48% hydrobromic acid were added and stirred overnight. Subsequently, the solution was cooled to -10 C. in an ice water bath, and a solution of 8.1 g (117.4 mmol) of sodium nitrite dissolved in 150 mL of water was added dropwise under conditions such that the temperature did not rise by 5 C. or more, and the diazotized The reaction solution was stirred at 5 C. or less for 1 hour to obtain a diazonium solution.Next, in a 1 L four-necked round bottom flask equipped with a stirrer, an Erlin condenser, a thermometer, and a 500 mL dropping funnel, 16.2 g (116.9 mmol) of cuprous bromide, 48% hydrobromic acid 38 mL and water 90 mL were added, and the mixture was cooled to 0 C. and stirred. Subsequently, the diazonium solution was added dropwise at a temperature not exceeding 5 C. and stirred at the same temperature for 30 minutes, then the temperature was raised to 40 C., and the mixture was stirred at the same temperature for 18 hours.200 mL of water was added to the obtained reaction solution, cooled to room temperature, and extracted twice with 200 mL of DCM. Then, the organic layer was washed with 100 mL of 5% sodium sulfite aqueous solution, then washed with 100 mL of saturated brine, dried with magnesium sulfate, magnesium sulfate was removed by suction filtration, and the solvent was distilled off under reduced pressure. Subsequently, the resulting crude product was purified by silica gel column chromatography using n-heptane as a developing solution to obtain 17.2 g (yield: 68.0%) of the desired bromide.
67% Sodium nitrite (4.4 g, 65 mmol) was dissolved in 40 ml of concentrated sulfuric acid at 0 C, and compound M-2 (10.6 g, 58 mmol) was dissolved in a small amount of glacial acetic acid and slowly dropped into the reaction solution to maintain the temperature. Below 5 C, after the completion of the dropwise addition, the temperature was kept at 0 C and stirring was continued for 2 hours. Diethyl ether (200 ml) was added to the reaction mixture for stirring, and a diazonium salt was precipitated and filtered to obtain a brown solid; another reaction flask was added with CuBr (12.5g, 87mmol), 48% HBr (300ml), Finally, the obtained brown diazonium salt is added, warmed to 66 C for 2 hours, cooled to room temperature, filtered, filter cake washed twice with water, the obtained solid Petroleum ether: Eluent of dichloromethane = 10:1 was passed through the column to afford intermediate (9.6 g, 67%).
Example 11 3-Bromodibenzofuran Combine N-dibenzofuran-3-ylamine (2.0 g, 10.8 mmol), water (20 ml), and conc. hydrobromic acid (6 ml). Cool to 0 C. Add a solution of sodium nitrite (0.7 g, 10.8 mmol) in water (16 ml). After 15 minutes add the mixture above to a mixture of copper bromide (1.7 g, 12.3 mmol) in water (9.2 ml) and hydrobromic acid (4 ml). Warm to ambient temperature. After 18 hours, add water and extract with dichloromethane, Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.
9.6 g Sodium nitrite (4.4g, 65mmol) was dissolved in 40ml when concentrated sulfuric acid, 3-amino-dibenzofuran (10.6g, 58mmol) was dissolved in a small amount of glacial acetic acid was slowly added dropwise to the reaction mixture, maintaining the temperature below 5 , 0 dropwise after incubation was continued stirring for 2 hours, 200ml of diethyl ether was added to the reaction solution was stirred with a diazonium salt and precipitation was filtered to give a brown solid; the other reaction flask was added CuBr (12.5g, 87mmol) , 300ml48% of HBr, brown diazonium salt was added last, temperature was raised to 66 deg.] C for 2 hours, cooled to room temperature, filtered, the filter cake washed twice with water, the resulting solid with petroleum ether: dichloromethane = 10: 1 eluent through the column, to give 9.6g solid

  • 10
  • [ 857594-84-4 ]
  • [ 26608-06-0 ]
  • 12
  • [ 19817-07-3 ]
  • [ 26608-06-0 ]
  • 3-dibenzofuran-3-ylethynyl-1-aza-bicyclo[2.2.2]octan-3-ol [ No CAS ]
  • 14
  • [ 26608-06-0 ]
  • [ 92151-88-7 ]
  • 18
  • [ 26608-06-0 ]
  • 7-nitro-dibenzofuran-3-carboxylic acid methyl ester [ No CAS ]
  • 20
  • [ 26608-06-0 ]
  • phenyl-carbamic acid dibenzofuran-3-yl ester [ No CAS ]
  • 21
  • [ 26608-06-0 ]
  • [ 10026-13-8 ]
  • [ 204440-73-3 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid; In chloroform; Step (b) 7-Bromo-dibenzofuran-2-sulfonyl Chloride Chlorosulfonic acid (3.75 mL, 56 mmoles) was added dropwise to a solution of <strong>[26608-06-0]3-bromo-dibenzofuran</strong> (9.21 g, 37.3 mmoles) in 150 mL of chloroform at room temperature. The reaction was stirred for 5 hours, cooled to 0 C., filtered, and washed the solid with cold dichloromethane. This solid (6.12 g, 18.7 mmoles) was mixed with phosphorous pentachloride (12.9 g, 61.7 mmoles) and the mixture was heated to 110 C. for 4 hours. The mixture was cooled to room temperature and quenched with ice water. Filtered the resulting suspension to give the title compound as a white solid.
  • 22
  • [ 540-80-7 ]
  • [ 4106-66-5 ]
  • [ 7789-45-9 ]
  • [ 26608-06-0 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; Step (a) 3-Bromo-dibenzofuran 3-Amino-dibenzofuran (15 g, 81.9 mmoles) was added in portions to a suspension of cupric bromide (21.9 g, 98.2 mmoles) and tert.-butyl nitrite (12.66 g, 122.8 mmoles) in 350 mL of acetonitrile. This mixture was heated to reflux for 2 hours and then stirred for 16 hours at room temperature. The reaction was partitioned between 1 M HCl and diethyl ether. The diethyl ether layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography gave the title compound as a yellowish solid.
  • 23
  • [ 26608-06-0 ]
  • [ 1499-21-4 ]
  • (Dibenzofuran-3-yl)-diphenylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; tert-butyl methyl ether; ethyl acetate; a) (Dibenzofuran-3-yl)-diphenylphosphine oxide (IV) A solution of 25 g of <strong>[26608-06-0]3-bromo-dibenzofuran</strong> in 90 ml of THF is added to a boiling mixture of 4.31 g of Mg and 10 ml of THF and the mixture is boiled under reflux for a further 1 hour. Subsequently a solution of 23.9 g of diphenylphosphinic chloride in 45 ml of THF is added dropwise at 0 C. and the mixture is stirred for a further 1 hour at room temperature. After neutralization of the reaction solution with 1N HCl, it is admixed with 150 ml of ethyl acetate and water and the organic phase is dried with MgSO4 and concentrated. The residue is stirred with tert-butyl methyl ether for 16 hours and filtered. 24.9 g of yellow crystals (65% of theoretical) remain as residue. m.p.: 151-155 C.
  • 24
  • [ 109-72-8 ]
  • [ 26608-06-0 ]
  • [ 2629-47-2 ]
  • 2-(C6H5)2SbC12H7O [ No CAS ]
  • 25
  • [ 26608-06-0 ]
  • C12H7BrMgO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium; In tetrahydrofuran; at 50 - 55℃; for 2 - 3h;Product distribution / selectivity; The title compound was prepared according to the following method. First in a similar manner to Preparative Example 11, 1 M NBS and AIBN were added to a carbon tetrachloride solution containing 0.5 mM of 2-hydroxydibenzofuran; the mixture was stirred for two hours and filtered under reduced pressure, to give 2-bromodibenzofuran. Then in a similar manner to Preparative Example 8, 0.3 mole of metal magnesium and 30 ml of THF were placed in a flask under a nitrogen environment; 2-bromodibenzofuran above was added thereto; the mixture was allowed to react at 55 C. for two hours, to give a Grignard reagent. The Grignard reagent was then added to a THF solution containing 0.5 mole of chlorotriethoxysilane, and the mixture was allowed to react at 20 C. for one hour. After reaction, the reaction solution was filtered under reduced pressure for removal of magnesium chloride, and THF and unreacted compound were removed from the filtrate, to give the title compound at a yield of 60%.Infrared absorption spectrum measurement of the compound obtained showed an absorbance derived from SiC bond at 1080 cm-1, indicating that the compound had a SiC bond.Further, nuclear magnetic resonance (NMR) measurement of the compound was performed.7.5 ppm (m) (4H, aromatic)7.5 ppm (m) (3H, aromatic)3.5 ppm (m) (6H, ethoxy group methylene group)1.6 ppm (m) (9H, ethoxy group methyl group)These results indicated that the compound obtained was the compound represented by General Formula (alphaII-1). Preparative Example 17Preparation of the Organic Silane Compound Represented by General Formula (alphaII-2)The title compound was prepared according to the following method. First, 0.5 mole of metal magnesium was added to a THF solution containing 0.5 M of the intermediate in Preparative Example 12, 2-bromodibenzofuran under a nitrogen atmosphere; the mixture was allowed to react at 50 C. for three hours, to give a Grignard reagent; 0.5 M of 1-bromonaphthalene was then added thereto; and the mixture was allowed to react at 20 C. for one hour, to give 3-naphthalen-2-yl-dibenzofuran.Further, 0.5 M of 3-naphthalen-2-yl-dibenzofuran above was added to a carbon tetrachloride solution containing 1 M NBS and AIBN, and the mixture was allowed to react at 55 C. for 2 hours, to give an intermediate (D). 0.5 M of chlorotriethoxysilane was added thereto, and the mixture was allowed to react at 20 C. for 2 hours, to give the title compound at a yield of 30%.Infrared absorption spectrum measurement of the compound obtained showed an absorbance derived from SiC bond at 1090 cm-1, indicating that the compound had a SiC bond.Further, nuclear magnetic resonance (NMR) measurement of the compound was performed.7.8 ppm (m) (4H, aromatic)7.5 ppm (m) (5H, aromatic)7.3 ppm (m) (2H, aromatic)7.2 ppm (m) (2H, aromatic)3.6 ppm (m) (6H, ethoxy group methylene group)1.5 ppm (m) (9H, ethoxy group methyl group)These results indicated that the compound obtained was the compound represented by General Formula (alphaII-2).Organic silane compounds different in acene skeleton number and organic silane compounds different in the group derived from the terminal fused polycyclic compound can be prepared by a similar method.
  • 26
  • [ 20279-16-7 ]
  • [ 26608-06-0 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h; The title compound was prepared according to the following method. First in a similar manner to Preparative Example 11, 1 M NBS and AIBN were added to a carbon tetrachloride solution containing 0.5 mM of 2-hydroxydibenzofuran; the mixture was stirred for two hours and filtered under reduced pressure, to give 2-bromodibenzofuran. Then in a similar manner to Preparative Example 8, 0.3 mole of metal magnesium and 30 ml of THF were placed in a flask under a nitrogen environment; 2-bromodibenzofuran above was added thereto; the mixture was allowed to react at 55 C. for two hours, to give a Grignard reagent. The Grignard reagent was then added to a THF solution containing 0.5 mole of chlorotriethoxysilane, and the mixture was allowed to react at 20 C. for one hour. After reaction, the reaction solution was filtered under reduced pressure for removal of magnesium chloride, and THF and unreacted compound were removed from the filtrate, to give the title compound at a yield of 60%.Infrared absorption spectrum measurement of the compound obtained showed an absorbance derived from SiC bond at 1080 cm-1, indicating that the compound had a SiC bond.Further, nuclear magnetic resonance (NMR) measurement of the compound was performed.7.5 ppm (m) (4H, aromatic)7.5 ppm (m) (3H, aromatic)3.5 ppm (m) (6H, ethoxy group methylene group)1.6 ppm (m) (9H, ethoxy group methyl group)These results indicated that the compound obtained was the compound represented by General Formula (alphaII-1).
  • 27
  • [ 26608-06-0 ]
  • [ 1201645-07-9 ]
  • [ 1201645-15-9 ]
YieldReaction ConditionsOperation in experiment
50% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; for 12h;Inert atmosphere; Reflux; A mixture of compound 34 (200mg, 0.44mmol, leq), <strong>[26608-06-0]3-bromodibenzofuran</strong> (118mg, 0.48mmol, l.leq), Pd (PPh3)4 (lOmg, O.OOdeltammol, 0.02eq), Na2CO3 (137mg, lJmmol, 3eq), toluene (1OmL) and H2O (2mL) was degassed, protected with N2, and refluxed for 12 hrs. After cooled to room temperature, the mixture was diluted with water, extracted with EA. The organic phase was dried over MgSO4 and filtered. The filtrate was concentrated and purified by column chromatography (silica gel) to give 35c, 2-(4-((6- (dibenzo[b,d]furan-3-yl)-3-m'troquinolm-4-yl)methyl) phenyl)- 2-methyl propanenitrile (156mg,: 50%).
  • 28
  • [ 26608-06-0 ]
  • Pd(dppf)2Cl2 [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1246562-66-2 ]
YieldReaction ConditionsOperation in experiment
With nitrogen; potassium acetate; triethylamine; In 1,4-dioxane; ethyl acetate; <strong>[26608-06-0]3-bromodibenzofuran</strong> (4.79 g, 19.39 mmol), bispinacolatodiboron (6.4 g, 25.2 mmol), KOAc (7.61 g, 77.54 mmol) was added to 100 mL of dioxane in a r.b. flask. Content was degassed for 30 minutes under bubbling nitrogen gas and Pd(dppf)2Cl2 (158 mg, 0.019 mmol) was added to the reaction mixture. After degassing for another 10 minutes, the reaction mixture was heated to 80 C. and stirred overnight. Reaction flask was then cooled to room temperature and filtered through a pad of celite. Deep brown color solution was then partitioned in between brine and ethyl acetate. Organic layer was collected, dried over anhydrous Na2SO4 and excess solvent was evaporated under vacuum. Brown colored solid was then dry loaded in silica gel column and quickly flashed with 5% ethylacetate/hexane/0.005% triethylamine to give 5.08 g final product. Synthesis of 2-(dibenzofuran-3-yl)pyridine.
  • 29
  • [ 5410-97-9 ]
  • [ 26608-06-0 ]
YieldReaction ConditionsOperation in experiment
palladium-carbon; In ethyl acetate; 3-nitrodibenzofuran (6.2 g, 29.08 mmol) was dissolved in 360 mL ethyl acetate and was degassed 5 minutes by passing nitrogen gas through the solution. 500 mg of Pd/C was added to the solution and the content was hydrogenated at 60 psi pressure. Reaction was let go until pressure in hydrogenation apparatus stabilizes at 60 psi for 15 minutes. Reaction content was then filtered through a small celite pad and off white color product was obtained. (5.3 g, 28.9 mmol) Synthesis of 3-bromodibenzofuran.
  • 30
  • [ 1285719-49-4 ]
  • [ 26608-06-0 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 185℃; for 1.5h; In argon atmosphere, a solution of Intermediate A-2 synthesized in the step (A-2) (561 g, 2.10 mol) and potassium carbonate (580 g, 4.20 mol) in N-methyl-2-pyrrolidone (NMP) (6 L) was stirred at 185 C. for 1.5 h. The reaction liquid was cooled and stirred after adding water. The generated solid matter was collected by filtration and washed with water. The obtained solid was dissolved into toluene and the insoluble was removed by filtration. The filtrate was concentrated. The crystal obtained by adding heptane was collected by filtration to obtain Intermediate A-3 (414 g). The yield was 80%.
60% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 180℃; for 3h; <Synthesis Example 26 (Synthesis of Intermediate 26)>; Under the atmosphere of argon gas, 1000 ml of toluene and 500 ml of 2 M concentration sodium carbonate aqueous solution was added to 120.0 g (399 mmol) of 1-bramo-3-fluaro-4-iodobromobenzene, 72.7 g (479 mmol) of 2-methoxyphenyl boronic acid sand 9.2 g (7.96 mmol) of tetrakis(triphenylphosphine) palladium (0), and the resultant mixture solution was heated while being refluxed for 10 hours. After the reaction was completed, extraction with toluene was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was condensed. The residue was subjected to a chromatography purification using a silica gel column to obtain 89.6 g of 4-bromo-2-fluoro-2'-methoxybiphenyl in the state of white crystal (yield: 80%). Under the atmosphere of argon gas, of 900 ml of dichloromethane was added to 89.6 g (319 mmol) of 4-bromo-2-fluoro-2'-methoxybiphenyl, and the resultant mixture solution was stirred while cooling with ice. After adding 95.9 g (382 mmol) of boron tribromide by dropping, the solution was stirred at a room temperature for 12 hours. After completion of the reaction, 200 ml of water was added, and the resultant mixture solution was stirred for 1 hour, followed by removing a water layer. After drying the organic layer over magnesium sulfate, the resultant was condensed. The residue was subjected to a chromatography purification using a silica gel column to obtain 68.1 g of 4-bromo-2-fluoro-2'-hydroxybiphenyl in the state of white crystal (yield: 70%). Onto 68.1 g (255 mmol) of 4-bromo-2-fluoro-2'-hydroxybiphenyl and 70.4 g (510 mmol) of potassium carbonate, 1500 ml of N-methylpyrrolidone was added and the resultant solution was stirred at 180C for 3 hours. After completion of the reaction, water was added and extraction by toluene was conducted. After drying an organic layer over sodium sulfate, the resultant was condensed. The resultant residue was re-crystallized through toluene and 44.2 g of 3-bromodibenzofuran in the state of white crystal was obtained (yields:60%). Under the atmosphere of argon gas, 350 ml of toluene and 170 ml of 2 M concentration sodium carbonate aqueous solution was added to 34.2 g (138 mmol) of 3-bromobenzofram, 26.0 g (166 mmol) of 4-chlorophenyl boronic acid and 3.2 g (2.77 mmol) of tetrakis(triphenylphasphine)palladium (0), and the resultant mixture solution was heated while being refluxed for 12 hours. After the reaction was completed, filtration was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was concentrated. The residue was subjected to a chromatography purification using a silica gel column to obtain 23.1 g of white crystal (yield:60%). The resultant white crystal was identified as Intermediate 26 from the result in accordance with the FD-MS analysis.
60% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 180℃; for 3h; 1,500 milliliters of N-methylpyrrolidone were added to 68.1 g (255 mmol) of 4-bromo-2-fluoro-2'-hydroxybiphenyl and 70.4 g (510 mmol) of potassium carbonate, and then the mixture was stirred at 180C for 3 hours. After the completion of the reaction, water was added to the resultant, and then extraction with toluene was performed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was recrystallized from toluene so as to be purified. Thus, 44.2 g of a white crystal of 3-bromodibenzofuran were obtained (in 60% yield) . The crystal was identified as Intermediate 1-37 by FD-MS analysis.
60% With 1-methyl-pyrrolidin-2-one; potassium carbonate; at 180℃; for 3h; 1, 500 mL of N-methylpyrrolidone were added to 68.1 g (255 mmol) of 4-bromo-2-fluoro-2'-hydroxybiphenyl and 70.4 g (510 mmol) of potassium carbonate, and then the mixture was stirred at 180C for 3 hours. After the completion of the reaction, water was added to the resultant, and then extraction with toluene was performed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was recrystallized from toluene so as to be purified. Thus, 44.2 g of a white crystal were obtained (in 60% yield). The crystal was identified as the Intermediate 27 by FD-MS analysis.
60% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 180℃; for 3h; Synthesis Example 5 (synthesis of intermediate 5)> Under an argon atmosphere, 1,000 mL of toluene and 500 mL of an 2M aqueous solution of sodium carbonate were added to 120.0 g of 1-bromo-3-fluoro-4-iodobenzene, 72.7 g of 2-methoxyphenylboronic acid, and 9.2 g of tetrakis(triphenylphosphine)palladium(0), and then the reaction mixture was heated at reflux for 10 hours. Immediately after the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 89.6 g of the white crystal of 4-bromo-2-fluoro-2'-methoxybiphenyl were obtained (in 80% yield). Under an argon atmosphere, 900 mL of dichloromethane were added to 89.6 g of 4-bromo-2-fluoro-2'-methoxybiphenyl, and then the mixture was stirred under ice cooling. 95.9 g of boron tribromide were added dropwise to the mixture, and then the whole was stirred at room temperature for 12 hours. After the completion of the reaction, 200 mL of water were added to the resultant, and then the mixture was stirred for 1 hour. After that, the aqueous layer was removed. The organic layer was dried with magnesium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 68.1 g of the white crystal of 4-bromo-2-fluoro-2'-hydroxybiphenyl were obtained (in 70% yield). 1,500 mL of N-methylpyrrolidone were added to 68.1 g of 4-bromo-2-fluoro-2'-hydroxybiphenyl and 70.4 g of potassium carbonate, and then the mixture was stirred at 180 C for 3 hours. After the completion of the reaction, water was added to the resultant, and then the mixture was extracted with toluene. The organic layer wasdriedwithsodiumsulfate, and was then concentrated. The residue was recrystallized from toluene and purified. Thus, 44.2 g of the white crystal of 3-bromodibenzofuran were obtained (in 60% yield) . The white crystal was identified as the intermediate 5 by FD-MS analysis.
60% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 180℃; for 3h; 1500 mL of N-methylpyrrolidone was added to 68.1 g of 4-buromo-2-fluoro-2?-hydroxybiphenyl (255 millimoles) and 70.4 g of potassium carbonate (510 millimoles), and the mixture was stirred for 3 hours at 180 C. After completion of a reaction, water was added and the mixture was subjected to extraction with toluene. The organic phase was dried with sodium sulfate and concentrated. The residual concentrate was purified by recrystallization from toluene to obtain 44.2 g of 3-buromodibenzofuran white crystals (yield 60%). The crystals were identified as Intermediate 6 by FD-MS analysis
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 180℃; for 3h; 68.1 Grams of 4-bromo-2-fluoro-2'-hydroxybiphenyl, 70.4 g of potassium carbonate, and 1,200 ml of N-methylpyrrolidone were loaded into a 2, 000-ml three-necked flask, and then the mixture was stirred at 180C for 3 hours. After the completion of the reaction, water was added to the resultant, and then extraction with toluene was performed. The organic layerwas dried with sodium sulfate, andwas then concentrated. The residue was recrystallized from toluene so as to be purified. Thus, 44.2 g of a white crystal of 3-bromodibenzofuran were obtained.

  • 31
  • [ 26608-06-0 ]
  • [ 1679-18-1 ]
  • [ 1267248-41-8 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 77℃; for 42h;Inert atmosphere; In argon atmosphere, a mixture of Intermediate A-3 synthesized in the step (A-3) (309 g, 1.25 mol), 4-chlorophenylboronic acid (353 g, 2.26 mol), tetrakis(triphenylphosphine) palladium(0) (29 g, 25 mmol), sodium carbonate (398 g, 3.76 mol), DME (1.9 L), and water (1.9 L) was stirred at 77 C. for 42 h. The reaction liquid was cooled to room temperature. After adding water, the reaction liquid was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain Intermediate B (255 g). The yield was 73%.
60% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 12h;Reflux; Inert atmosphere; <Synthesis Example 26 (Synthesis of Intermediate 26)>; Under the atmosphere of argon gas, 1000 ml of toluene and 500 ml of 2 M concentration sodium carbonate aqueous solution was added to 120.0 g (399 mmol) of 1-bramo-3-fluaro-4-iodobromobenzene, 72.7 g (479 mmol) of 2-methoxyphenyl boronic acid sand 9.2 g (7.96 mmol) of tetrakis(triphenylphosphine) palladium (0), and the resultant mixture solution was heated while being refluxed for 10 hours. After the reaction was completed, extraction with toluene was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was condensed. The residue was subjected to a chromatography purification using a silica gel column to obtain 89.6 g of 4-bromo-2-fluoro-2'-methoxybiphenyl in the state of white crystal (yield: 80%). Under the atmosphere of argon gas, of 900 ml of dichloromethane was added to 89.6 g (319 mmol) of 4-bromo-2-fluoro-2'-methoxybiphenyl, and the resultant mixture solution was stirred while cooling with ice. After adding 95.9 g (382 mmol) of boron tribromide by dropping, the solution was stirred at a room temperature for 12 hours. After completion of the reaction, 200 ml of water was added, and the resultant mixture solution was stirred for 1 hour, followed by removing a water layer. After drying the organic layer over magnesium sulfate, the resultant was condensed. The residue was subjected to a chromatography purification using a silica gel column to obtain 68.1 g of 4-bromo-2-fluoro-2'-hydroxybiphenyl in the state of white crystal (yield: 70%). Onto 68.1 g (255 mmol) of 4-bromo-2-fluoro-2'-hydroxybiphenyl and 70.4 g (510 mmol) of potassium carbonate, 1500 ml of N-methylpyrrolidone was added and the resultant solution was stirred at 180C for 3 hours. After completion of the reaction, water was added and extraction by toluene was conducted. After drying an organic layer over sodium sulfate, the resultant was condensed. The resultant residue was re-crystallized through toluene and 44.2 g of <strong>[26608-06-0]3-bromodibenzofuran</strong> in the state of white crystal was obtained (yields:60%). Under the atmosphere of argon gas, 350 ml of toluene and 170 ml of 2 M concentration sodium carbonate aqueous solution was added to 34.2 g (138 mmol) of 3-bromobenzofram, 26.0 g (166 mmol) of 4-chlorophenyl boronic acid and 3.2 g (2.77 mmol) of tetrakis(triphenylphasphine)palladium (0), and the resultant mixture solution was heated while being refluxed for 12 hours. After the reaction was completed, filtration was carried out immediately and a water layer was removed. After drying the organic layer over sodium sulfate, the resultant was concentrated. The residue was subjected to a chromatography purification using a silica gel column to obtain 23.1 g of white crystal (yield:60%). The resultant white crystal was identified as Intermediate 26 from the result in accordance with the FD-MS analysis.
60% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 12h;Inert atmosphere; Reflux; <Synthesis Example 2-21 (synthesis of Intermediate 2-21) > Under an argon atmosphere, 350 mL of toluene and 170 mL of an aqueous solution of sodium carbonate having a concentration of 2 M were added to 34.2 g (138 mmol) of Intermediate 2-20, 26.0 g (166 mmol) of 4-chlorophenyl boronic acid, and 3.2 g (2.77 mmol) of tetrakis(triphenylphosphine)palladium(0), and then the mixture was heated while being refluxed for 12 hours. Immediatelyafterthe completionof the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 23.1 g of a white crystal were obtained (in 60% yield). The crystal was identified as Intermediate 2-21 by FD-MS analysis.
60% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 12h;Inert atmosphere; Reflux; Under an argon atmosphere, 350 mL of toluene and 170 mL of an aqueous solution of sodium carbonate having a concentration of 2 M were added to 34.2 g (138 mmol) of the Intermediate 27, 26.0 g (166 mmol) of 4-chlorophenylboronic acid, 3.2 g (2.77 mmol) of tetrakis (triphenylphosphine)palladium (0), and then the mixture was heated for 12 hours while being refluxed. Immediatelyafter the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 23.1 g of a white crystal were obtained (in 60% yield). The crystal was identified as the Intermediate 28 by FD-MS analysis.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 12h;Inert atmosphere; Reflux; Under an argon atmosphere, 34.2 g of <strong>[26608-06-0]3-bromodibenzofuran</strong>, 26.0 g of 4-chlorophenyl boronic acid, 3.2 g of tetrakis(triphenylphosphine)palladium, 350 ml of toluene, and 170 ml of an aqueous solution of sodium carbonate having a concentration of 2 M were loaded into a 1,000-ml three-necked flask, and then the mixture was heated for 12 hours while being refluxed. Immediately after the completion of the reaction, the resultant was filtrated, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate, and was then concentrated. The residue was purified by silica gel column chromatography. Thus, 23.1 g of a white crystal were obtained. The crystal was identified as the intermediate-17' by FD-MS analysis.

 

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