4-Methyl-3-(trifluoromethyl)benzoic acid → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

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To a solution of sodium bromate (1109 mg, 7.35 mmol) in H2O (3.3 mL) was added 4-methyl-3-trifluoromethyl-benzoic acid (500 mg, 2.449 mmol) in ethyl acetate (5 mL), followed by a solution of sodium bisulfite (765 mg, 7.35 mmol) in H2O (9 mL) over a period of about 15 min. The mixture was stirred overnight at room temperature and overnight at 50° C. The mixture was poured in ether (50 mL). The aqueous layer was extracted twice with ether and the combined organic layer was washed with anhydrous Na2S2O3 solution, dried, filtered and concentrated in vacuo to give the crude 4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 35 (563 mg, 81%) which was used without further purification. (m/z)=282 and 284 (M+H)+.

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