Reaction #9728

Reaction equation

triphenylphosphine

ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate

intermediate 19

ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate

dichloromethane water

carbon tetrabromide

→

title compound

Ethyl(2E)-3-[4-(bromomethyl)-2-methylphenyl]prop-2-enoate

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherthe organic phase separated
2. 2
   Washwashed with more water, brine
3. 3
   Dryingdried over sodium sulfate
4. 4
   Otherthen evaporated in vacuo
5. 5
   OtherThe isolated product was further purified by flash column chromatography

Procedure

A solution of ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate (intermediate 19, 1.389 g) in dry dichloromethane (40 ml) was cooled to 0° C. and treated with carbon tetrabromide (2.3 g) followed by, in small portions, triphenylphosphine (1.82 g). The resulting solution was stirred thus overnight, then poured into dichloromethane/water and the organic phase separated and washed with more water, brine and dried over sodium sulfate then evaporated in vacuo. The isolated product was further purified by flash column chromatography using cyclohexane:ethyl acetate (9:1) as an eluent which gave the title compound as a white solid.

Source