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Chemical Structure| 61079-72-9 Chemical Structure| 61079-72-9
Chemical Structure| 61079-72-9

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CAS No.: 61079-72-9

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Product Details of [ 61079-72-9 ]

CAS No. :61079-72-9
Formula : C7H3F3O2
M.W : 176.09
SMILES Code : O=C(O)C1=CC=C(F)C(F)=C1F
MDL No. :MFCD00061232
InChI Key :WEPXLRANFJEOFZ-UHFFFAOYSA-N
Pubchem ID :302932

Safety of [ 61079-72-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 61079-72-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 33.28
TPSA ?

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

37.3 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.12
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

1.75
Log Po/w (WLOGP)?

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

3.06
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.

2.9
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

2.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.27

Water Solubility

Log S (ESOL):?

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

-2.34
Solubility 0.808 mg/ml ; 0.00459 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.15
Solubility 1.25 mg/ml ; 0.00707 mol/l
Class?

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

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

-2.61
Solubility 0.436 mg/ml ; 0.00248 mol/l
Class?

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

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

 No
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

 No
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.

-6.13 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.

0.56

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

1.0 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<1.0
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)

 1.4

Application In Synthesis of [ 61079-72-9 ]

* 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 [ 61079-72-9 ]

[ 61079-72-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 61079-72-9 ]
  • [ 197520-71-1 ]
YieldReaction ConditionsOperation in experiment
97.1% With sulfuric acid; nitric acid; at 90 - 95℃; for 3.5h; A stirred solution of 2,3,4-trifluorobenzoic acid (5) (10 g, 56.8 mmol) in concentrated H2SO4 (98%, 33.0 g) was treated dropwise with the mixture of concentrated HNO3 (65%, 6.0g) and H2SO4 (98%, 6.3g) for 3.5 h between 90 and 95 C. The reaction progress was monitored by TLC (30% ethylacetate in hexane). After completion of the reaction, the reaction mixture was cooled to room temperature and ice-water (50g) was added. The precipitation was separated by centrifugation and dried between 50 and 55 C for 8 h. The crude product was purified by column chromatography using 20% ethylacetate:hexane as eluent. The solvent was removed under reduced pressure to afford a white solid 6 (12.2 g) in 97.1% yield.
92% With sulfuric acid; nitric acid; for 2.5h; A 3 litre three neck round bottom flask was charged with 125 ml H2SO4. Fuming nitric acid was added (8.4 ml, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid (25 g, 142 mmol) was added in 5 g portions over 90 minutes. The dark brownish yellow solution was stirred for 60 minutes at which time the reaction was complete. The reaction mixture was poured into 1 litre of an ice: water mixture and extracted with diethyl ether (3 x 600 ml). The combined extracts were dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid was suspended in hexanes and stirred for 30 min after which time it was filtered to give 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (-) m/z 220 (M-I) detected.
92% With sulfuric acid; nitric acid; for 2.5h; A 3 liter three neck round bottom flask is charged with 125 ml H2SO4. Fuming nitric acid is added (8.4 ml, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid 1 (25 g, 142 mmol) is added in 5 g portions over 90 minutes. The dark brownish yellow solution is stirred for 60 min at which time the reaction is complete. The reaction mixture is poured into 1 liter of an ice:water mixture and extracted with diethyl ether (3×600 ml). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid is suspended in hexanes and stirred for 30 min after which time it is filtered to give 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (-) m/z 220 (M-1) detected.
92% With sulfuric acid; nitric acid; for 2.5h; 2, 3,4-Trifluoro-5-nitro-benzoic acid 2A 3 liter three neck round bottom flask is charged with 125 ml H2504. Fuming nitricacid is added (8.4 ml, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid 1(25 g, 142 mmol) is added in 5 g portions over 90 minutes. The dark brownish yellow solutionis stirred for 60 mm at which time the reaction is complete. The reaction mixture is poured into 1 liter of an ice:water mixture and extracted with diethyl ether (3 x 600 ml). The combinedorganic extracts are dried (Mg504) and concentrated under reduced pressure to give a yellow solid. The solid is suspended in hexanes and stirred for 30 mm after which time it is filtered togive 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (-) nilz 220 (M-1) detected.
88% With sulfuric acid; nitric acid; at 90℃; for 5h; Compound 1 (5 g, 28.41 mmol) was added to a solution of concentrated sulfuric acid (15 ml) and heated to 90 C.Then, a mixed acid of concentrated H2SO4 (3.2 g, 98%) and HNO3 (3 g, 68%) was added dropwise, and reacted for 5 hours.After cooling to room temperature, the mixture was poured into EtOAc (EtOAc)EtOAc.An oil of 5.5 g was obtained in a yield of 88%.
78% With sulfuric acid; nitric acid; In water; Step a Preparation of 5-nitro-2,3,4-trifluorobenzoic acid To gently stirring concentrated sulfuric acid (50 ml) was added fuming nitric acid (3.4 ml, 0.076 mol). Solid 2,3,4-trifluorobenzoic acid (10.00 g, 0.05565 mol) was added directly in increments. After stirring 45 minutes, the reaction mixture had become an orange homogeneous solution which was then poured over chilled water (400 ml). The resulting aqueous suspension was extracted with diethyl ether (3*200 ml). The combined extracts were dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 12.30 g of a dull, light-yellow solid. Recrystallization from chloroform (50 ml) afforded 9.54 g of the pale yellow microcrystalline product; 78% yield; m.p.; 1H-NMR (400 MHz; DMSO)delta 14.29 (broad s, 1H), 8.43-8.38 (m, 1H); 13C-NMR (100 MHz; DMSO) delta162.41, 154.24 (dd, JC-F=270.1, 10.7 Hz), 148.35 (dd, JC-F=267.0, 9.2 Hz), 141.23 (dt, JC-F=253.4 Hz), 133.95,1 23.30 (d, JC-F=2.2 Hz), 116.92 (dd, JC-F=18.2, 3.8 Hz); 19F-NMR (376 MHz; DMSO) delta-120.50 to -120.63 (m), -131.133 to -131.27 (m), -153.63 to -153.74 (m).
78% With sulfuric acid; nitric acid; In water; Step a Preparation of 5-Nitro-2,3,4-trifluorobenzoic Acid To gently stirring concentrated sulfuric acid (50 ml) was added fuming nitric acid (3.4 ml, 0.076 mol). Solid 2,3,4-trifluorobenzoic acid (10.00 g, 0.05565 mol) was added directly in increments. After stirring 45 minutes, the reaction mixture had become an orange homogeneous solution which was then poured over chilled water (400 ml). The resulting aqueous suspension was extracted with diethyl ether (3*200 ml). The combined extracts were dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 12.30 g of a dull, light-yellow solid. Recrystallization from chloroform (50 ml) afforded 9.54 g of the pale yellow microcrystalline product; 78% yield; m.p.; 1H-NMR (400 MHz; DMSO) delta14.29 (broad s, 1H), 8.43-8.38 (m, 1H); 13C-NMR (100 MHz; DMSO) delta162.41, 154.24 (dd, JC-F=270.1, 10.7 Hz), 148.35 (dd, JC-F=267.0, 9.2 Hz), 141.23 (dt, JC-F=253.4 Hz), 133.95, 123.30 (d, JC-F=2.2 Hz), 116.92 (dd, JC-F=18.2, 3.8 Hz); 19F-NMR (376 MHz; DMSO) delta-120.50 to -120.63 (m), -131.133 to -131.27 (m), -153.63 to -153.74 (m).
78% With sulfuric acid; nitric acid; In water; Step a: Preparation of 5-nitro-2,3,4-trifluorobenzoic acid To gently stirring concentrated sulfuric acid (50 ml) was added fuming nitric acid (3.4 ml, 0.076 mol). Solid 2,3,4-trifluorobenzoic acid (10.00 g, 0.05565 mol) was added directly in increments. After stirring 45 minutes, the reaction mixture had become an orange homogeneous solution which was then poured over chilled water (400 ml). The resulting aqueous suspension was extracted with diethyl ether (3 x 200 ml). The combined extracts were dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 12.30 g of a dull, light-yellow solid. Recrystallization from chloroform (50 ml) afforded 9.54 g of the pale yellow microcrystalline product; 78 % yield; m.p.;1H-NMR (400 MHz; DMSO) delta 14.29 (broad s, 1H), 8.43-8.38 (m, 1H); 13C-NMR (100 MHz; DMSO) delta 162.41, 154.24 (dd, JC-F=270.1, 10.7 Hz), 148.35 (dd, JC-F=267.0, 9.2 Hz), 141.23 (dt, JC-F=253.4 Hz), 133.95, 123.30 (d, JC-F=2.2 Hz), 116.92 (dd, JC-F=18.2, 3.8 Hz); 19F-NMR (376 MHz; DMSO) delta-120.50 to -120.63 (m), -131.133 to -131.27 (m), -153.63 to -153.74 (m).
78% With sulfuric acid; nitric acid; In water; Step a: Preparation of 5-nitro-2,3,4-trifluorobenzoic acid To gently stirring concentrated sulfuric acid (50 ml) was added fuming nitric acid (3.4 ml, 0.076 mol). Solid 2,3,4-trifluorobenzoic acid (10.00 g, 0.05565 mol) was added directly in increments. After stirring 45 minutes, the reaction mixture had become an orange homogeneous solution which was then poured over chilled water (400 ml). The resulting aqueous suspension was extracted with diethyl ether (3 x 200 ml). The combined extracts were dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 12.30 g of a dull, light-yellow solid. Recrystallization from chloroform (50 ml) afforded 9.54 g of the pale yellow microcrystalline product; 78 % yield; m.p.;1H-NMR (400 MHz; DMSO) delta 14.29 (broad s, 1H), 8.43-8.38 (m, 1H); 13C-NMR (100 MHz; DMSO) delta 162.41, 154.24 (dd, JC-F=270.1, 10.7 Hz), 148.35 (dd, JC-F=267.0. 9.2 Hz), 141.23 (dt, JC-F=253.4 Hz), 133.95, 123.30 (d, JC-F=2.2 Hz), 116.92 (dd, JC-F=18.2, 3.8 Hz); 19F-NMR (376 MHz; DMSO) delta-120.50 to -120.63 (m), -131.133 to -131.27 (m), -153.63 to -153.74 (m).
78% With sulfuric acid; nitric acid; for 0.75h; To gently stirring concentrated sulfuric acid (50 ml) was added fuming nitric acid (3.4 ml, 0.076 mol). Solid 2,3,4-trifluorobenzoic acid (10.00 g, 0.05565 mol) was added directly in increments. After stirring 45 minutes, the reaction mixture had become an orange homogeneous solution which was then poured over chilled water (400 ml). The resulting aqueous suspension was extracted with diethyl ether (3*200 ml). The combined extracts were dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 12.30 g of a dull, light-yellow solid. Recrystallization from chloroform (50 ml) afforded 9.54 g of the pale yellow microcrystalline product; 78% yield; m.p.; 1H-NMR (400 MHz; DMSO) delta 14.29 (broad s, 1H), 8.43-8.38 (m, 1H); 13C-NMR (100 MHz; DMSO) delta 162.41, 154.24 (dd, JC-F=270.1, 10.7 Hz), 148.35 (dd, JC-F=267.0, 9.2 Hz), 141.23 (dt, JC-F=253.4 Hz), 133.95, 123.30 (d, JC-F=2.2 Hz), 116.92 (dd, JC-F=18.2, 3.8 Hz); 19F-NMR (376 MHz; DMSO) delta -120.50 to -120.63 (m), -131.133 to -131.27 (m), -153.63 to -153.74 (m).
75% With sulfuric acid; nitric acid; at 0 - 20℃; for 6h; Example 1; Preparation of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H- benzoimidazole-5-carboxylic acid; [00238] Step A; 2,3,4-Trifluoro-5-mtrobenzoic acid; Fuming HNO3 90% (549.0 g,7.84 mol corrected for 90% wt, 1.26 equiv.) was added to 2.0 L (3.35 kg) of concentrated H2SO4 over 18 minutes with stirring. The solution OfHNO3 was then added to a mixture of 2,3,4-trifluorobenzoic acid (1094 g, 6.21 mol, 1 equiv.) in 3.3 L (5.85 kg) of concentrated H2SO4 in a second flask with ice- water bath cooling over an hour. When addition was complete, the reaction solution was allowed to warm to room temperature. After 5 hours, the reaction was complete as determined by HPLC and the reaction mixture (brown solution) was poured into a mechanically stirred mixture of 10.6 kg of distilled water and 11.8 kg of ice over 10 minutes. The yellow slurry was cooled to 14 C, stirred for 2 hours and then filtered. The cake was rinsed with 4.0 L of distilled water and then with 5 L of heptane. The wet cake was oven-dried overnight. The crude solids (1.791 kg) were then stirred in 16 L of distilled water (9 vol.), filtered and oven-dried at 55 0C under high vacuum overnight to yield 1035.9 g (75%) of 2,3,4-trifluoro-5-nitrobenzoic acid as a yellowish solid. HPLC was 98 a% (220 nm) and 100% (254 nm). 1H NMR (400 MHz, DMSO-d6) delta 8.44 (IH, apparent dt, J 1.9, 7, Ar-H); 19F NMR (376 EPO <DP n="51"/>MHz, DMSOd6) delta -153.9, -131.5, -120.9. 13C NMR (100 MHz, DMSO-d6) delta 117 (C, m), 124 (CH, b s), 134 (C, s), 141 (C-F, dt, J251, 10), 148 (C-F, dd, J 265, 13), 154 (C-F, dd, J 265, 10), 163 (COOH). IR v^/cnf1 3108 (br), 1712, 1555, 1345, 1082. MS APCI (-) m/z 220 (M-I) detected.
75% With sulfuric acid; nitric acid; at 0 - 20℃; for 6.3h;Product distribution / selectivity; Fuming HNO3 90% (549.0 g,7.84 mol corrected for 90% wt, 1.26 equiv.) was added to 2.0 L (3.35 kg) of concentrated H2SO4 over 18 minutes with stirring. The solution Of HNO3 was then added to a mixture of 2,3,4-trifluorobenzoic acid (1094 g, 6.21 mol, 1 equiv.) in 3.3 L (5.85 kg) of concentrated H2SO4 in a second flask with ice-water bath cooling over an hour. Upon complete addition, the reaction mixture was allowed to warm to room temperature. After 5 hours, the reaction was complete by HPLC and the reaction mixture (brown solution) was poured over 10 minutes into a mechanically stirred mixture of 10.6 kg of distilled water and 11.8 kg of ice. The yellow slurry was cooled to 14 C, stirred for 2 hours and then filtered. The cake was rinsed with 4.0 L of distilled water and then with 5 L of heptane. The wet cake was oven- dried overnight. The crude solids (1.791 kg) were then stirred in 16 L of distilled water (9 vol.), filtered and oven-dried at 55 0C under high vacuum overnight to yield 1035.9 g (75%) of compound 2 as a yellowish solid. HPLC was 98 a% (220 nm) and 100% (254 nm). 1H NMR (400 MHz, d6 DMSO) delta 8.44 (IH, apparent dt, J 1.9, 7, Ar-H). 19F NMR (376 MHz, d6 DMSO) delta -153.9, -131.5, -120.9. 13C NMR (100 MHz, d6 DMSO) delta 117 (C, m), 124 (CH, b s), 134 (C, s), 141 (C-F, dt, 7251, 10), 148 (C-F5 dd, J265, 13), 154 (C-F, dd, J265, 10), 163 (COOH). IR vmJcmA 3108 (br), 1712, 1555, 1345, 1082. MS APCI (-) m/z 220 (M-I) detected.
74.3% With Hexamethyldisiloxane; sulfuric acid; nitric acid; at 15 - 25℃; for 6.25h;Product distribution / selectivity; Trifluorobenzoic acid (70 Kg5 398 MoI) in sulphuric acid (96 wt%; 194 L) and hexamethyldisiloxane (6,5 Kg5 40 MoI)5 at 23 0C, was added a 1:1 mixture of sulphuric acid (96 wt%) and nitric acid (98 wt%) (total 70.1 Kg)5 over 75 min. The temperature of the reaction mixture was maintained between 15 and 25 0C during the addition. The mixture was stirred for a further 5 hours and then run onto ice (700 Kg)5 keeping the temperature of the ice micture below 0 C. Water (35 L) was used to rinse the nitration reactor into the quench reactor and the obtained mixture was stirred for 2 hours at 0 0C5 then isolated on a centrifuge. The resultant wet cake was washed with cold water (350 L)5 and the solid was then suspended in water (280 L) and stirred for 2 hours at 0 C. This suspension was then centrifuged and the cake was washed with cold water (210 L), then dried in a vacuum oven at 45 0C for 2 days, to provide 2,354-Trifluoro-5-nitro benzoic acid (69.4 Kg5 74.3% yiled). 1H NMR (400 MHz5 d6 DMSO) delta 8.44 (IH, apparent dt, J 2, 7, Ar-H). 19F NMR (376 MHz, d6 DMSO) delta -153.9, -131.5, -120.9. 13C NMR (100 MHz5 d6 DMSO) delta 117 (C, m), 124 (CH, b s), 134 (C, s), 141 (C-F, dt, J251, 10), 148 (C-F5 dd, J265, 13), 154 (C-F, dd, J265, 10), 163 (COOH). IR vmjcm l 3108 (br), 1712, 1555, 1345, 1082. MS APCI (-) m/z 220 (M-I) detected.
50% With sulfuric acid; nitric acid; In sulfuric acid; at 5 - 20℃; for 2h; Example 1 5-FLUORO-6-(2-FLUORO-4-IODO-DHENYLAMINO)-3-METHYL-3H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID (2-- OH-ETHOXY)-AMIDE Step A: Preparation of 2. 3. 4-trifluoro-5-nitrobenzoic acid Fuming HNO3 was added dropwise to the cold (5 TO-10 C) conc. H2SO4 (5L) and stirred in a three-necked round bottom flask (20L), maintaining the temperature between 5 to- 10 C. Then was added 2, 3, E-TRIFTUOROBENZOIC acid (1 kg, 5.6 mol) in portions, maintaining the temperature at 5O C and after completion of the addition the reaction mixture was allowed to warm to room temperature, stirred for 2h and (the suspension becomes light yellow solution) then poured into 30 kg of crushed ice. The mixture was extracted with ether (3 X 4.0 L) and the organic extracts were washed with water (2 X 2L), brine (2.0 L), dried over anhydrous MGS04, filtered and evaporated under vacuum. The residue (cream colored solid) obtained is re-crystallized from hot chloroform provided the title compound as a solid (yellow). Yield : 880G (50%), mp. 128-129 OC
With sulfuric acid; nitric acid; for 2.5h; Example 1; Step A: 2,3,4-Trifluoro-5-nitro-benzoic acid 2 . A 3 liter three neck round bottom flask is charged with 125 mL H2SO4. Fuming nitric acid is added (8.4 mL, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid 1 (25 g, 142 mmol) is added in 5 g portions over 90 minutes. The dark brownish yellow solution is stirred for 60 minutes at which time the reaction is complete. The reaction mixture is poured into 1 liter of an ice:water mixture and extracted with diethyl ether (3×600 mL). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid is suspended in hexanes and stirred for 30 minutes after which time it is filtered to give 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (-) m/z 220 (M-1) detected.
29 g (92%) With sulfuric acid; nitric acid; Step A 2,3,4-Trifluoro-5-nitro-benzoic acid A 3 liter three neck round bottom flask is charged with 125 ml H2SO4. Fuming nitric acid is added (8.4 ml, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid (25 g, 142 mmol) is added in 5 g portions over 90 minutes. The dark brownish yellow solution is stirred for 60 min at which time the reaction is complete. The reaction mixture is poured into 1 liter of an ice:water mixture and extracted with diethyl ether (3*600 ml). The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid is suspended in hexanes and stirred for 30 min after which time it is filtered to give 29 g (92%) of clean desired product as an off-yellow solid.
With sulfuric acid; potassium nitrate; In hexane; (1) 2,3,4-Trifluoro-5-nitrobenzoic acid: 2,3,4-Trifluorobenzoic acid (1 g) was added to sulfuric acid (5 ml), and potassium nitrate (630 mg) was gradually added to the mixture under cooling on ice. The resultant mixture was stirred overnight at room temperature, and the reaction mixture was poured onto crushed ice. The mixture was extracted with diethyl ether, and the organic phase was dried over magnesium sulfate. The solvent was removed through distillation, and n-hexane was added to the residue, to thereby collect the solid of the title compound (1 g) by filtration. Form: colorless powder Melting point: 127-135 C. 1 H--NMR(CDC kappa3)delta; 8.67-8.71(m, 1H)
With potassium nitrate; In hexane; sulfuric acid; Referential Example 5 Synthesis of 2,3,4-Trifluoro-5-nitrobenzoic Acid 2,3,4-Trifluorobenzoic acid (2.5 g) was dissolved in concentrated sulfuric acid (15 ml). Potassium nitrate (1.62 g) was added to the solution under ice cooling. The temperature of the reaction mixture was (given back to room temperature to conduct stirring for 2 days. The reaction mixture was poured into ice water (300 ml) and extracted with ether (200 ml). An organic layer was dried and concentrated. Hexane was added to the residue to conduct filtration, thereby obtaining the title compound (3.06 g) as a pale yellow powder. 1 H-NMR (d6 -DMSO) delta: 8.40-8.47(m,1H).
With sulfuric acid; nitric acid; at 5 - 20℃; for 2h; 00128] Step A: 2,3,4-Trifluoro-5-nitrobenzoic acid:[00129] Fuming nitric acid (1.7 ml) is added dropwise to concentrated sulfuric acid (25 ml) while maintaining the temperature at 5 - 10 C. 2,3,4-Trifluorobenzoic acid (5 g, 28 mmoles) is added in small portion to this solution while keeping the reaction temperature at 5 C. After completion the reaction mixture is stirred at room temperature for an additional 2 hours and poured into ice. The mixture is extracted with ether (3 x 75 ml). The organic layers are combined, washed with brine, dried (MgSO4). The solvent is removed, and the crude product is recrystallized from hot chloroform to obtain the title compound.

  • 2
  • [ 61079-72-9 ]
  • ice-water [ No CAS ]
  • [ 197520-71-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; Reference Example 1 A mixed solution of 10.56 g (60 mmol) of 2,3,4-trifluorobenzoic acid and 15.6 ml of sulfuric acid was ice-cooled, and 11.4 ml of a fumed nitric acid was added dropwise thereto at 5 to 30 C. and the mixture was stirred at the same temperature for 5 hours to complete the reaction. After completion of the reaction, the resulting reaction mixture was added to 400 ml of ice-water, and then, extracted twice with 150 ml of ethyl acetate. The combined organic layers were washed with 100 ml of water, dried over anhydrous magnesium sulfate, and then, filtered and evaporated to dryness. The resulting product obtained by evaporation to dryness was added to 50 ml of water and the mixture was stirred to wash the product. After collecting the precipitates by filtration, the precipitates were dried under reduced pressure to obtain 10.0 g (45.2 mmol) of 2,3,4-trifluoro-5-nitrobenzoic acid. Melting point: 134-135 C. 1 H-NMR (DMSO, 400 MHz) delta (ppm)=8.68 (H, ddd, Ar-H)
  • 3
  • [ 61079-72-9 ]
  • [ 284030-57-5 ]
 

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