To a solution of 4-bromoaniline (40 g, 0.232 mol) and triethylamine (32 mL) in dichloromethane (200 mL) was slowly added hydrocinnamoyl chloride (37.5 g, 0.223 mol) dropwise at 0 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was poured into water and 10% hydrochloric acid solution was added. The white solid slurry formed was stirred for 1 hour under cooling in an ice bath. The solid product was separated by filtration, washed with ether and dried in air to afford N-(4-bromophenyl)-3-phenylpropanamide (62 g, 92% yield).
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