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

Participants

Reaction Steps

Table 1, Entry 2. In the reaction tube were mixed 4-bromobenzonitrile (0.182 g, 1.0 mmol), methyl acrylate (0.108 g, 1.25 mmol), palladium acetate (0.00225 g, 0.01 mmol), tri-o-tolylphosphine (0.0122 g, 0.04 mmol), triethylamine (0.127 g, 1.25 mmol) and 0.50 ml DMF.under nitrogen. The contents of the flask were irradiated for 3.50 min with an effect of 60 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml DCM. The combined extracts were washed with 25 ml water and concentrated to an oil. The crude product was purified by column chromatography on silica gel using i-hexane/diethyl ether (1/1) as the eluent. The yield was 94% (pale yellow crystals).

Provenance & Evidence