Benzyl Bromide → 4-Benzyloxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-cyanophenol (5.0 g, 42 mmol), benzylbromide (8.6 g, 50 mmol), potassium carbonate (11.6 g, 84.0 mmol) in DMF (40 mL) was stirred at 100° C. for 3 h. The precipitate was filtered off and the filtrate was diluted with EtOAc and washed with water. The organic layer was dried (Na2SO4) and concentrated. The resulting crude product was purified by silica gel column chromatography (eluting with petroleum ether/EtOAc from 20/1 to 5/1) to give 4-(benzyloxy)benzonitrile as a white solid (8.1 g, 92%).

Provenance & Evidence