Benzyl Bromide → 1-(Benzyloxy)-3-bromobenzene

Participants

Reaction Steps

To a stirred solution of bromomethylbenzene (24.39 g, 143 mmol), 3-bromophenol (24.92 g, 144 mmol) in acetone (20 ml) was added potassium carbonate (59.72 g, 430 mmol). The suspension was refluxed overnight and then evaporated. To the residue was added H2O (100 ml) and extracted with EtOAc (3×80 ml). The combined EtOAc extracts were back washed with Na2CO3 and then dried over MgSO4, filtered and evaporated to get an off-white solid, which was purified via flash column chromatography (10% CH2Cl2 in hexane) to give 1-benzyloxy-3-bromo-benzene as a white solid (10 g, 67%): 1HNMR (DMSO-d6) 7.46-7.00 (m, 9H, Ar), 5.12 (s, 2H, CH2). The product was carried over to the next step.

Provenance & Evidence