4-Methoxybenzyl alcohol → 4-Methoxybenzyl bromide

Participants

Reaction Steps

3.0 g (0.0217 mol) of p-methoxybenzyl alcohol were dissolved in 50 ml of ether and treated with 14.4 g (0.0433 mol) of carbon tetrabromide. 11.4 g (0.0433 mol) of triphenyl-phosphine were added while cooling with ice. The mixture was stirred at room temperature for 3 hrs. After removal of the solvent the residue was filtered over a short silica gel column with ether/hexane (1:1) as the eluent. The filtrate was subjected to a bulb-tube distillation. 2.05 g (47%) of 4-methoxybenzyl bromide were obtained as a colorless oil; b.p. 120°-140°(22 Torr). MS: me/e (% basic peak)=202, 200 (C8H9BrO+, 3), 121 (C8 H9O+, 100).

Provenance & Evidence