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

Participants

Reaction Steps

3,3-Dimethylacryloyl chloride (Intermediate 1, 4.16 g, 35.1 mmol) was slowly added to a solution of 4-bromoaniline (Intermediate 2, 5.00 g, 29.2 mmol) in 25 mL of methylene chloride. 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 then poured on 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 as a yellow solid (7.43 g, 100% yield).

Provenance & Evidence