4-Bromoaniline → 2-Butenamide, N-(4-bromophenyl)-3-methyl-

Participants

Reaction Steps

3,3-Dimethylacryloyl chloride (available from Aldrich, 4.16 g, 35.1 mmol) was slowly added to a solution of 4-bromoaniline (5.00 g, 29.2 mmol) in 25 mL of dichloromethane. After stirring at room temperature for 20 min triethylamine (2.5 mL) was added dropwise to the mixture. The resulting solution was stirred at room temperature for 3 h and poured to 100 mL of ice-water mixture. The organic layer was separated, washed with brine (2×20 mL), dried (MgSO4) and concentrated at reduced pressure to give a yellow residue. Purification by flash chromatography (90:10 hexane/ethyl acetate) afforded the title compound (7.43 g, 100% yield) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.34 (s, 4H), 7.1 (bs, 1H), 5.69 (s, 1H), 2.23 (s, 3H), 1.91 (s, 3H).

Provenance & Evidence