Acrylic acid, 2-(hydroxymethyl)-, ethyl ester → Ethyl 2-(fluoromethyl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(hydroxymethyl)acrylate (3.0 g, 23.1 mmol) in dichloromethane (40 mL) cooled to −78° C., was added DAST (3.32 mL, 25.4 mmol). The reaction mixture was stirred at −78° C. for 30 minutes and then at ambient temperature for 1 hour. The reaction was quenched with water (40 mL) and the layers were separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford ethyl 2-(fluoromethyl)acrylate (2.54 g, 83%).

Provenance & Evidence