Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

Participants

Reaction Steps

4-Bromophenol (3.9 g, 22.41 mmol), benzyl bromide (4.6 g, 26.9 mmol), and cesium carbonate (89.6 mmol) were combined in DMSO (30 mL) under nitrogen at room temperature. The reaction was stirred for 24 h, filtered to remove the solids, and then partitioned between ethyl acetate and water. The organic layer was washed with water, 1 N HCl, and brine; dried over magnesium sulfate; and, concentrated to give a semi-solid. The product was crystallized from hexanes to give 1-bromo-4-benzyloxy-benzene as an off white powder (4.3 g, 75%). MS found: (M+H)+=263, 265.

Provenance & Evidence