2-Bromo-4-trifluoromethoxyaniline

461-82-5

175278-17-8

General procedure for the synthesis of 2-bromo-4-trifluoromethoxyaniline from 4-(trifluoromethoxy)aniline: N-bromosuccinimide (3.62 g, 20.34 mmol) was slowly added to a solution of 4-(trifluoromethoxy)aniline (3.00 g, 16.9 mmol) in acetonitrile (30 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography using 10% ethyl acetate/hexane as eluent to give 2-bromo-4-trifluoromethoxyaniline as a brown oil (3.6 g, 83% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.11 (broad single peak, 2H), 6.73 (double peak, 1H), 6.99 (double-double-heavy peak, 1H), and 7.31 (double-heavy peak, 1H).The LC-MS analysis showed that the [M-H]- peak was located at m/z 253.1.