Triethylamine → 1,1-Dimethylethyl 3-(3-formylphenyl)-2-propenoate

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 3-bromobenzaldehyde (20 g), tert butyl acrylate (40 mL), triethylamine (44 mL) and tris(2-methylphenyl)phosphine (3.4 g) in dry dimethylformamide (300 mL) is added palladium (II) acetate in one portion. The resulting dark brown mixture is heated at 100° C. for 18 hours then evaporated in vacuo. The residual semi-solid is partitioned between ethyl acetate (250 mL) and 2 N hydrochloric acid (250 mL). the organic phase is washed three times with water (250 mL), dried over magnesium sulphate and evaporated. The resulting dark brown oil (28.1 g) is purified by flash chromatography on silica eluting initially with a mixture of cyclohexane and dichloromethane (4:1 v/v) then with a mixture of cyclohexane and dichloromethane (1:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give tert-butyl 3-(3-formylphenyl)acrylate as a yellow oil (14.08 g).

Provenance & Evidence