Carbon Dioxide → 3-cyano-2-fluoro-4-methoxybenzoic acid

Participants

Reaction Steps

To a stirred lithium diisopropylamide solution (1.8M in heptane/THF/ethylbenzene, 44.1 mL, 79.4 mmol) at −50° C. was added a solution of 2-fluoro-6-methoxybenzonitrile (10 g, 66.16 mmol) in THF (80 mL) slowly and stirring was continued at that temperature for 1 h. The reaction mixture was poured onto a stirred slurry of dry ice in dry THF (100 mL). After the mixture had warmed up to room temperature, it was concentrated to about 50 mL, diluted with 6 N HCl (200 mL), extracted with dichloromethane, dried with sodium sulfate, concentrated, and dried in vacuo to give 3-cyano2-fluoro-4-methoxybenzoic acid (12.9 g, 100%).

Provenance & Evidence