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With water; sodium hydroxide In methanol at 20℃; for 1.5 h;
To a solution of methyl 4-chloro-3-(trifluoromethoxy)benzoate (3.1 g, 12.18 mmol) in methanol (30 mL) was added a solution of sodium hydroxide (1.46 g, 36.50 mmol) in water (10 mL) at room temperature, and the reaction mixture was stirred for 1.5 h at room temperature. The solution was adjusted to pH 4 with HC1 (36 percent). The resulting solution was extracted with ethyl acetate (3 x 100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated in vacuo to afford 4-chloro-3- (trifluoromethoxy)benzoic acid as a light yellow solid (2.10 g, 74percent). LC/MS (ES, m/z): [M+H]+ 241.0 *H NMR (300 MHz, DMSO) δ 7.92 - 7.99 (m, 2H), 7.40 - 7.47 (m, 1H)
To a solution of <strong>[457097-93-7]methyl 4-amino-3-(trifluoromethoxy)benzoate</strong> (5 g, 25.33 mmol) in CH3CN (100 mL) was added concentrated HC1 (20 mL) in an ice/water bath. This was followed by the addition of a solution of NaN02 (5.9 g, 85.51 mmol) in water (20 mL) dropwise at 0-5C. The reaction was stirred for 40 min at 0C in an ice/water bath. To this was added copper chloride (5.9 g, 59.60 mmol) in portions at 0C. The resulting solution was stirred for 1.5 min at 0C in a water/ice bath maintained under an inert atmosphere of nitrogen. The resulting solution was extracted with ethyl acetate (3 x 100 mL) and the organic layers combined and dried in an oven under reduced pressure. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 : 100) to afford methyl 4-chloro-3- (trifluoromethoxy)benzoate as yellow oil (3 g, 55%).LC/MS (ES, m/z) [M+H]+ 255.0 *H NMR (300 MHz, DMSO) 57.91 - 7.99 (m, 2H), 7.56 (d, J (s, 3H)
With water; sodium hydroxide; In methanol; at 20℃; for 1.5h;
To a solution of methyl 4-chloro-3-(trifluoromethoxy)benzoate (3.1 g, 12.18 mmol) in methanol (30 mL) was added a solution of sodium hydroxide (1.46 g, 36.50 mmol) in water (10 mL) at room temperature, and the reaction mixture was stirred for 1.5 h at room temperature. The solution was adjusted to pH 4 with HC1 (36 %). The resulting solution was extracted with ethyl acetate (3 x 100 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated in vacuo to afford 4-chloro-3- (trifluoromethoxy)benzoic acid as a light yellow solid (2.10 g, 74%). LC/MS (ES, m/z): [M+H]+ 241.0 *H NMR (300 MHz, DMSO) delta 7.92 - 7.99 (m, 2H), 7.40 - 7.47 (m, 1H)
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