Dimethylformamide → 3-(4-Fluorophenyl)-2-propenamide

Participants

Reaction Steps

4-fluorocinnamic acid (25 g) was suspended in dichloromethane (300 ml); under ice cooling and stirring, DMF (0.5 ml) and then oxalyl chloride (15.36 ml) were added drop by drop; the same temperature was kept for 3 hours and gradually returned to room temperature. Under reduced pressure, the solvent was distilled off; the residue was dissolved in ethyl acetate (100 ml). This solution was added drop by drop to an ice-cooled mixed solution of 25% aqueous ammonia (250 ml) and ethyl acetate (52.5 ml). The reaction mixture was extracted with ethyl acetate (400 ml×2) and washed with saturated saline, after which it was dried over anhydrous magnesium sulfate. Under reduced pressure, the solvent was distilled off; the precipitated crystal was collected by filtration and dried to yield (E)-3-(4-fluorophenyl)-2-propenamide (24.4 g).

Provenance & Evidence