N-bromobutanimide → 5-bromo-4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one (1.1 g, 5.0 mmol) in DMF (20 mL) was added NBS (1.07 g, 6.0 mmol) in small portions over 15 min. The reaction mixture was stirred at room temperature for 20 min. Analysis by HPLC/MS indicated the starting 4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one was consumed, and about 17% (based on the UV absorption) of the desired product had formed. The reaction mixture was partitioned between water (50 mL) and EtOAc (50 mL). The resulting suspension was filtered, and the collected solid was washed with water, the dried in a vacuum oven at 50° C. for 16 h to afford 250 mg (17%) of the title compound as an off-white solid. HPLC/MS: retention time=3.35 min, [M+H]+=298.2.

Provenance & Evidence