3-(Trifluoromethyl)aniline → 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

3-Trifluoromethylaniline (1.6 g, 10 mmol) was dissolved in dichloromethane with DIEA (3.4 mL, 20 mmol), cooled to 0° C., and to this solution bromoacetyl chloride was added as a neat liquid (exothermic). After 1 hour the reaction mixture was washed with 1N HCl, dried and concentrated to a brown oil which was purified by column chromatography (10 to 40% EtOAc/hexanes) to give a light brown oil, 1.8 g, 6.4 mmol, 64% yield. 1H NMR (500 MHz, CDCl3) δ 8.19 (s, 1H), 7.75 (s, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.41 (t, J=7.9 Hz, 1H), 7.35 (d, J=7.8 Hz, 3.96 (s, 2H).

Provenance & Evidence