Water → Methyl 2-(bromomethyl)benzoate

Participants

Reaction Steps

A water jacketted, immersion photolysis vessel equipped with a N2 inlet, dropping funnel and a reflux condenser was charged with 1 L of carbon tetrachloride and 127 g. (0.847 mol) of 2-methyl toluate (Pfaltz and Bauer M29200). A solution of 400 ml carbon tetrachloride and 43.5 ml (0.849 mol) of bromine was added to the dropping funnel. After the solution had been heated to reflux the bromine solution was slowly added while the solution was irradiated with a 600 watt incandescent lamp. After the addition of the bromine solution was complete, the lamp was turned off and the solution cooled. The carbon tetrachloride was removed under reduced pressure. The resultant oil was crystallized from 250 ml of a (1:1) solution of diethyl ether and hexane. The solid was collected and washed with hexane to yield 119 g. (61%) of product.

Provenance & Evidence