N-bromobutanimide → Ethyl 5-(bromomethyl)-2-phenyl-1,3-oxazole-4-carboxylate

Participants

Reaction Steps

A solution of ethyl 5-methyl-2-phenyloxazole-4-carboxylate (11.0 g, 48 mmol), NBS (8.5 g, 48 mmol), and BPO (100 mg) in CCl4 (200 ml) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography to give ethyl 5-(bromomethyl)-2-phenyloxazole-4-carboxylate as a tan solid (5.2 g, 35% yield).

Provenance & Evidence