N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-5-fluorobenzo[d]oxazole-7-carboxylate

Participants

Reaction Steps

To methyl 5-fluoro-2-p-tolylbenzo[d]oxazole-7-carboxylate (420 mg, 1.47 mmol) in CCl4 (5 mL) was added NBS (262 mg, 1.47 mmol) and BPO (69 mg, 0.735 mmol), the resulting mixture was heated to reflux for 24 hr; then the solvent was evaporated and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=100:1-50:1) to obtain methyl 2-(4-(bromomethyl)phenyl)-5-fluorobenzo[d]oxazole-7-carboxylate as a white solid (350 mg, yield 65%). LC-MS (ESI) m/z 264 [M+1]+.

Provenance & Evidence