Sodium Carbonate → HCID 59518017, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4′-bromo-3′-nitroacetophenone (600 mg, 2.46 mmol), vinylboronic acid dibutyl ester (680 mg, 3.69 mmol), and sodium carbonate (1.83 g, 17.22 mmol) in THF/H2O (12 mL/4 mL) is added dichlorobis(triphenylphospine) palladium (II) (86 mg, 5% mmol). The reaction tube is sealed and the mixture is purged with N2 for 3 min and heated at 70° C. for 1.5 h. Then the mixture is cooled to room temperature and poured into saturated ammonia chloride aqueous solution. The mixture is extracted with ethyl acetate (3×20 mL). The organic extracts are combined, washed with brine and concentrated. The crude product is purified with silica gel column chromatography (20% ethyl acetate in hexanes) to afford 1-(3-Nitro-4-vinyl-phenyl)-ethanone as a yellow solid, 87% yield: ESMS m/z 192.0 (M+H+).

Provenance & Evidence