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

Participants

Reaction Steps

To a stirred solution of benzyl bromide (24.39 g, 142.6 mmol) and 3-bromo phenol (24.92 g, 144 mmol) in 20 mL of fresh acetone was added potassium carbonate (59.72 g, 432 mmol). The suspension was refluxed overnight. The mixture was evaporated and added water (100 mL), extracted with EtOAc (3×80 mL). The combined EtOAc extracts were back washed with water (100 mL), dried over MgSO4, filtered and evaporated to give 1-benzyloxy-3-bromo-benzene as an off-white solid (10.0 g, 67% yield): 1H NMR (DMSO-d6) δ 5.12 (s, 2H, CH2), 7.00-7.46 (m, 9H, Ar). The product was used in the next step without further purification.

Provenance & Evidence