3-(Phenylmethoxy)benzenemethanol → 3-Benzyloxybenzyl bromide

Participants

Reaction Steps

A solution of 3-benzyloxybenzyl alcohol (9.54 g) in methylene chloride (40 ml) with TMSBr (2.5 eq, 13 mL) was heated at reflux for 1 hr. After cooling, the reaction was concentrated and then reconcentrated 2 × with methylene chloride (40 ml). The residue was chromatographed on silica gel eluting first with hexane followed by 10% methylene chloride in hexane to afford 3-benzyloxybenzyl bromide which solidifies on cooling . 5.75 g m.p. 38°-40°.

Provenance & Evidence