Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

Participants

Reaction Steps

To a solution of 4-bromophenol (8.65 g, 50 mmol) in dimethylsulfoxide (100 mL) was added potassium t-butoxide (6.45 g, 57.5 mmol) and the mixture was stirred for 20 mins. Benzyl bromide (10.26 g, 60 mmol) was then added and the reaction was stirred for 1 hr. It was then diluted with brine (150 mL) and extracted with ethylacetate (3×200 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was distilled under vaccuum (0.8 mm Hg) to afford 13.17 g of 4-benzyloxybromobenzene as a white solid (b.p. 150°-155° C.).

Provenance & Evidence