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

Participants

Reaction Steps

To a stirred solution of 3-bromophenol (9.50 g, 54.9 mmol) in degassed DMF (150 mL) at 0° C., under argon, was added Cs2CO3 (35.8 g, 109 mmol). The resulting mixture was stirred for 1 hour, then benzyl bromide (10.3 g, 60.2 mmol) was added and stirring was continued for 2 hours at 0° C. The solvent was removed under reduced pressure, and the residue was partitioned between 20% aqueous NaOH (250 mL) and CHCl3 (500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting first with two column volumes of hexane, then with hexane—2% EtOAc to yield the desired product as a white solid.

Provenance & Evidence