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In methanol; diethyl ether; dichloromethane; at 0℃; for 0.333333h;
To a solution of <strong>[67515-55-3]4-fluoro-3-(trifluoromethyl)benzoic acid</strong> Ia (1.04 g, 5 mmol) in DCM/MeOH (4: 1, 10 mL) at 0 0C was added drop-wise a solution OfTMSCHN2 (2.0 M <n="119"/>in ether, 2.6 mL, 5.1 mmol). The reaction mixture was stirred at 00C until the colorless solution started to turn light yellow and maintained its light yellow color. The reaction was stirred for an additional 20 minutes then a few drops of acetic acid was added to quench the last few drops OfTMS-CHN2 (the solution turns colorless from light yellow). The solvent was removed in vacuo to give a crude product which was used directly for next step. MS (ESI, M-HH+) = 223.0
A solution of <strong>[67515-55-3]4-fluoro-3-(trifluoromethyl)benzoic acid</strong> (260 mg, 1.25 mmol, 1 eq) in MeOH (0.5 ml_) and CH2CI2 (2 ml_) was treated with TMSCHN2 (2M in hexanes, 0.85 ml_, 1.70 mmol, 1.4 eq) dropwise with stirring at room temperature. After the reaction was stirred for 10 min, acetic acid was added until the yellow color disappeared. The mixture was concentrated to afford methyl 4-fluoro-3- (trifluoromethyl)benzoate, which was used in the next step without further purification.
a Methyl 4-fluoro-3-trifluoromethylbenzoate 5 g of <strong>[67515-55-3]4-fluoro-3-trifluoromethylbenzoic acid</strong> and 9 ml of SOCl2 are stirred at 60 C. for 8 h in 50 ml of MeOH. The volatile constituents are then removed in vacuo and 5.1 g of a colorless oil are obtained, which is further employed without purification. Rf (EA/MeOH 10:1)=0.74 MS (DCl) 223 (M+H)+
With thionyl chloride; In methanol;
a) Methyl 4-fluoro-3-trifluoromethylbenzoate 5 g of <strong>[67515-55-3]4-fluoro-3-trifluoromethylbenzoic acid</strong> and 9 ml SOCl2 were stirred in 50 ml of MeOH at 60 C for 8 h. The volatile constituents were then removed in vacuo to result in 5.1 g of a colorless oil, which was employed further without purification. Rf(EA/MeOH 10:1)=0.74 MS (DCI) 223
To a stirred solution of <strong>[67515-55-3]4-fluoro-3-(trifluoromethyl)benzoic acid</strong> (10.0 g, 48.1 mmol) in MeOH (100 mL) was added cone. H2S04 (4 mL, 73.4 mmol) in drops at ambient temperature and the mixture was refluxed for 5 hours. 200 mL of aqueous solution of NaHC03 was added to basified the mixture, and the resulted mixture was extracted with EA (100 mL X 3). The combined extracts were washed with brine (100 mL X 2), dried, concentrated to obtain the title product (9.4 g, yield: 88%) as a light yellow oil. 1H MR (400 MHz, CDC13) delta 8.33 (dd, J = 6.8, 1.6 Hz, 1H), 8.28 - 8.22 (m, 1H), 7.28 (t, 1H), 3.95 (s, 3H).
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