N-bromobutanimide → 4-Bromo-3-(trifluoromethoxy)aniline

Participants

Reaction Steps

A solution of 3-trifluoromethoxy-aniline (1.77 g) in toluene (20 ml) was treated with N-bromosuccinimide (1.87 g) at ambient temperature and the reaction mixture was stirred for 2 hours at ambient temperature, quenched by addition of water and the mixture extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated), dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 95:5) to afford 4-bromo-3-trifluoromethoxy-aniline (270 mg) and 2-bromo-5-trifluoromethoxy-aniline (1.45 g), which were both characterized by mass and NMR spectra. 4-bromo-3-trifluoromethoxy-aniline: MS (ES+) 256/258 (MH+); 1H NMR (400 MHz, CDCl3) 3.5 (brs, 2H), 6.5 (d, 1H), 6.7 (s, 1H), 7.3 (d, 1H). 2-bromo-5-trifluoromethoxy-aniline: MS (ES+) 256/258 (MH+); 1H NMR (400 MHz, CDCl3) 4.2 (brs, 2H), 6.5 (d, 1H), 6.6 (s, 1H), 7.4 (d, 1H).

Provenance & Evidence