N-bromobutanimide → 2-Methoxy-4-(bromomethyl)-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

2-Methoxy-4-methyl-N-(methylsulfonyl)benzamide (Preparation 24, 500 mg, 2.06 mmol), N-bromosuccimide (402 mg, 2.36 mmol), azobisisobutyronitrile (10 mg, 0.06 mmol) and carbon tetrachloride (20 mL) were combined and stirred at reflux under nitrogen, whilst being irradiated with light from a lamp for 1 hour. After cooling, the mixture was evaporated, the residue suspended in water (30 mL) and extracted with EtOAc (1×30 mL). The organic layer was separated, washed with saturated brine (2×20 mL), dried over sodium sulfate, filtered and evaporated to give a solid, which was triturated with diethyl ether:hexane (1:4) to yield the title compound as a white solid (375 mg, 57%).

Provenance & Evidence