Benzyl Alcohol → 1-Bromo-4-phenylmethoxybenzene

Participants

Reaction Steps

To a solution of 1.07 g (26.8 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (80 ml) was added 4.02 g (21.5 mmol) of benzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. To the reaction mixture was then added 4.47 g (17.9 mmol) of 4-bromobenzyl bromide, and the mixture was allowed to react at room temperature for 19 hours. To the reaction mixture at 0° C. was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:2) yielded 4.61 g (16.6 mmol) of 4-bromophenyl benzyl ether.

Provenance & Evidence