Water → 3,4-Bis(benzoyloxymethyl)benzyl bromide

Participants

Reaction Steps

40 g (106 mmol) of 2-benzoyloxymethyl-4-hydroxymethylbenzyl benzoate are placed in 500 ml of dichloromethane and 77.6 g (234 mmol) of carbon tetrabromide in a round-bottomed flask and under a stream of nitrogen. At 0° C., a solution of 61.3 g (233 mmol) of triphenylphosphine in 200 ml of dichloromethane is added dropwise. The mixture is allowed to warm to room temperature over 2 hours. The reaction medium is poured into water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30) to give 32.6 g (70%) of the expected product in the form of a white powder.

Provenance & Evidence