4-(Methylthio)aniline → 2-Bromo-4-(methylthio)aniline

Participants

Reaction Steps

To a solution containing 1.0 mL (8.0 mmol) of 4-(methylthio)aniline in 40 mL of a 3:1 solution mixture of acetonitrile/carbon tetrachloride was added 1.6 g (8.8 mmol) of N-bromosuccinimide. The reaction mixture was heated to reflux for 30 min, then cooled to ambient temperature and concentrated in vacuo. To the residue was added 100 mL of ethyl acetate and the organic solution was washed sequentially with saturated aqueous sodium bicarbonate solution and saturated aqueous brine (100 mL each), dried over sodium sulfate, filtered and evaporated in vacuo to yield a viscous oil. The crude material was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 30% ethyl acetate/hexanes gradient) to give the title compound. 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.15 (dd, J=8.3, 2.0 Hz, 1H), 6.72 (d, 8.5 Hz, 1H), 4.08 (bs, NH2), 2.44 (s, 3H).

Provenance & Evidence