Methyl Acrylate → methyl (E)-3-(4-cyanophenyl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromobenzonitrile (25 g, 0.136 mol) and methylacrylate (58.6 g, 0.682 mol) in dry DMF (250 mL) was added PPh3 (2.8 g, 0.0106 mol), Pd(OAc)2 (1.3 g, 0.00579 mol), sodium bicarbonate (18 g, 0.214 mol) and triethylamine (25 mL). The reaction mixture was heated to 100° C. for 16 h under nitrogen. The reaction mixture was cooled and the solid was filtered off. The filtrate was diluted with water (1 L) and the product was extracted with diethyl ether (4×200 ml). The combined organic layer was washed with water, brine, dried and evaporated to yield the crude product which was purified by chromatography (SiO2, PetEther/EtOAc (9.5/0.5) as eluent) to yield the title compound as a liquid (18 g, 71%). TLC: PetEther/EtOAc (9.5/0.5); Rf: 0.75

Provenance & Evidence