Phosphorus tribromide → Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-

Participants

Reaction Steps

To a solution of 15.04 g (62 mmol) of 2-benzyloxy-3-hydroxymethyl-1-methoxybenzene, from Step 2, in 140 mL of diethyl ether at 0° C. was added slowly, with stirring, 2.9 mL (31 mmol) of phosphorous tribromide. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to ambient temperature over a 4 h period. The solution phase was decanted and the reaction was quenched with aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 12.48 g (65% yield) of the title compound.

Provenance & Evidence