Triethylamine → Ethyl 3-(4-cyanophenyl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromobenzonitrile (50 g, 0.275 mol) and ethyl acrylate (35.4 g, 0.412 mol) in dry DMF (250 mL), palladium acetate (0.61 g, 0.0027 mol), tris-o-tolylphosphine (3.34 g, 0.011 mol) and triethylamine (57.3 mL, 0.412 mol) were added and refluxed at 95-100° C. for 2 h under an argon atmosphere. The reaction was quenched by adding water (250 mL) and extracted with ether (3×250 mL). The combined extract was washed with 1.5 N HCl (250 mL), water and brine and dried over sodium sulfate (anhydrous). Solvent evaporation under reduced pressure and purification by column chromatography over neutral alumina, using ethyl acetate in petroleum ether as eluent, yielded 55 g (90%) of the sub-title compound as an off-white solid.

Provenance & Evidence