Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(4-bromo-3-methylphenyl)acrylate

Participants

Reaction Conditions

Reaction Steps

2.1 g (6.45 mmol, 1.5 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 900 mg of 4-bromo-3-methylbenzaldehyde in 5 ml of toluene. The reaction mixture is heated at 90° C. for 1 hour. The solvent is evaporated off and the residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate). 610 mg of methyl (E)-3-(4-bromo-3-methylphenyl)acrylate are obtained in oil form. Yield=55% over steps a, b and c.

Provenance & Evidence