반응 #9728

반응 방정식

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

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the organic phase separated
2. 2
   세척washed with more water, brine
3. 3
   건조dried over sodium sulfate
4. 4
   기타then evaporated in vacuo
5. 5
   기타The isolated product was further purified by flash column chromatography

실험 절차

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.

출처