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[ CAS No. 146137-72-6 ] {[proInfo.proName]}

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Chemical Structure| 146137-72-6
Chemical Structure| 146137-72-6
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Product Details of [ 146137-72-6 ]

CAS No. :146137-72-6 MDL No. :MFCD07371506
Formula : C7H4FIO Boiling Point : -
Linear Structure Formula :- InChI Key :DUCCBZWPROUBNU-UHFFFAOYSA-N
M.W : 250.01 Pubchem ID :11096976
Synonyms :

Safety of [ 146137-72-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 146137-72-6 ]

* 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 [ 146137-72-6 ]

[ 146137-72-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 2365-48-2 ]
  • [ 146137-72-6 ]
  • [ 146137-85-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dimethyl sulfoxide; at 20 - 70℃; for 5h;Inert atmosphere; General procedure: The crude starting material (10) was dissolved in DMSO (25 mL) and methyl thioglycolate (2.6 mL, 1.1 equiv.) was added dropwise under Ar at RT. Triethylamine (7.45 mL, 2.2 equiv.) was then added and the mixture was heated at 70 C for 5 hours. The reaction mixture was cooled to RT and poured slowly into vigorously stirred ice-water (250 mL). After 30 min of stirring, a light yellow precipitate was collected by filtration, rinsed with H2O, and dried in vacuo to afford a crude yellow solid (6.40 g, 80% crude yield). The product was used for the next reaction without further purification.
  • 2
  • [ 1121-86-4 ]
  • [ 68-12-2 ]
  • [ 146137-72-6 ]
YieldReaction ConditionsOperation in experiment
66% Step:1 To a solution of l -fluoro-3-iodobenzene (5.00 g, 22.5 mmol) in THF (50 mL), was added lithium diisopropylamide (17.0 mL, 33.7 mmol) dropwise at -78 C. After being stirred at -78 C for 2 hours, N N-dimethylformamide (4.90 g, 67.5 mmol) was added and the resulting mixture was stirred at -78 C for another 30 min. The reaction mixture was then treated with aq. solution of ammonium chloride (20 mL) and water (30 mL), extracted with diethyl ether (3 x 30 mL). The combined organic layers were washed with 2 Nu hydrochloric acid (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (100:1 to 50:1) to give the desired product (3.7 g, 66% yield). lU NMR (DMSO-i? , 500 MHz): delta 10.01 (s, 1H), 7.89 - 7.79 (m, 1H), 7.44 - 7.40 (m, 2H).
66% Step 1: To a solution of 1 -fluoro-3-iodobenzene (5.00 g, 22.5 mmol) in THF (50 mE), was added lithium diisopropylamide (17.0 mE, 33.7 mmol) dropwise at -78 C. After being stirred at -78 C. for 2 hours, N,N-dimethylformamide (4.90 g, 67.5 mmol) was added and the resulting mixture was stirred at -78 C. for another 30 mm. The reaction mixture was then treated with aq. solution of ammonium chloride (20 mE) and water (30 mE), extracted with diethyl ether (3x30 mE). The combined organic layers were washed with 2 N hydrochloric acid (20 mE) and brine (20 mE), dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with petroleuml ethyl acetate (100:1 to 50:1) to give the desired product (3.7 g, 66%yield). 1HNMR(DMSO-d5, 500MHz): oe 10.01 (s, 1H),7.89-7.79 (m, 1H), 7.44-7.40 (m, 2H).
Buthyllithium (1.6 M, 60 ml, 0.113 mol) is added to an ice cooled solution of diisopropyl- amine (17.6 ml, 0.124 mol) in THF (200 ML). The solution is stirred at 0C for 30 minutes and is cooled TO-78 OC. I-FLUORO-3-IODO-BENZENE (25 g, 0.113 mol) in THF (20 ML) is slowly added to the preformed LDA mixture. The resulting solution is stirred for another hour after which DMF (9.55 ml, 0.124 mol) is added and stirring is continued for another 30 minutes at - 78 C. The reaction is quenched first with acetic acid (20 ml) followed by water (200 ML). The mixture is extracted with ether. The organic layer is washed with a 2N HCI solution, brine, is dried over MGS04 and evaporated to afford the desired compound (28.3 g).
General procedure: To a stirred solution of 1-fluoro-2-iodobenzene (4.6 mL, 39 mmol) in THF (39 mL)at -78C was added 1.8 M LDA solution (22.8 mL, 1.05 equiv.) dropwise over 10 minunder Ar. After 10 min, DMF (3.65 mL, 1.2 equiv.) was added dropwise and the reactionwas stirred for 10 min at -78C. The reaction was quenched at -78C by the rapid additionof 10 mL of acetic acid followed by 80 mL of H2O. The cooling bath was removed, andthe aqueous phase was extracted with diethyl ether (70 mL x 3). The organic layers werecombined and washed with 0.5 N HCl solution (150 mL x 2), H2O (150 mL x 2), and brine(150 mL). The organic solution was dried over MgSO4, filtered, and concentrated underreduced pressure. The resulting brown solid (6.25 g, 64% crude yield) was dried in vacuoand used for the next reaction without further purification.

  • 3
  • [ 88284-48-4 ]
  • [ 146137-72-6 ]
  • [ 1514-16-5 ]
  • 4
  • [ 146137-72-6 ]
  • 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate [ No CAS ]
  • 1-fluoro-6,7-dimethyl-9H-fluoren-9-one [ No CAS ]
  • 5
  • [ 146137-72-6 ]
  • [ 885522-11-2 ]
  • 6
  • [ 146137-72-6 ]
  • [ 60-34-4 ]
  • 4-iodo-1-methyl-1H-indazole [ No CAS ]
  • 7
  • [ 146137-72-6 ]
  • C21H18N4O [ No CAS ]
  • 8
  • [ 146137-72-6 ]
  • C22H20N4O [ No CAS ]
  • 9
  • [ 146137-72-6 ]
  • <i>N</i>-(4-iodo-benzo[<i>b</i>]thiophene-2-carbonyl)-guanidine [ No CAS ]
  • 10
  • [ 146137-72-6 ]
  • [ 768-60-5 ]
  • 8-fluoro-3-(4-methoxyphenyl)isoquinoline 2-oxide [ No CAS ]
  • 11
  • [ 79544-29-9 ]
  • [ 146137-72-6 ]
  • 12
  • [ 146137-72-6 ]
  • [ 334971-50-5 ]
YieldReaction ConditionsOperation in experiment
59% To a mixture of <strong>[146137-72-6]2-iodo-6-fluorobenzaldehyde</strong> (45 mmol) in H2O (22.5 ml), EtOH (22.5 ml), and ice (20 g) was added hydroxylamine hydrochloride (3.19 g, 49.5 mmol, 1.1 eq.). Then, 112.5 mmol of 50% NaOH (4.5 g in 4.5 ml H2O, 2.5 eq.) was added with stirring. Enough ice to keep the temperature at 25-30 C. was added. The reaction was stirred for 2 h, acidified with conc. HCl to pH 4 (ice was added to keep the temperature at 25-30 C.), and extracted with Et2O. The combined organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel using ethyl acetate in hexanes (5%-10%) to give <strong>[146137-72-6]2-iodo-6-fluorobenzaldehyde</strong> oxime (7.06 g, 59% over 2 steps) as an oil that solidified over time. [00425] 1H NMR (400 MHz, CDCl3) delta 8.67 (br s, 1H), 8.29 (s, 1H), 7.71 (d, 1H) 7.14 (t, 1H), 7.06-7.01 (m, 1H). MS (ES) (m/z) 265.9 [M+1].
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Technical Information

? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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