Carbon Dioxide → 2-(4-Cyano-3-(trifluoromethyl)phenyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide (13.8 mL, 24.8 mmol, 1.8M in THF) was added to 4-methyl-2-(trifluoromethyl)benzonitrile (2.30 g, 12.4 mmol) in THF (20 mL) at −78° C. and stirred for 5 minutes at −78° C. Excess solid carbon dioxide was added then the mixture was stirred at room temperature for 17 hours. Saturated aqueous ammonium chloride (10.5 mL) and EtOAc (20 mL) was added and the aqueous layer was acidified with 1M HCl. The mixture was extracted with EtOAc (3×15 mL) and the combined organic phases were dried over sodium sulphate and evaporated in vacuo to afford the title compound as a brown oil (88%, 2.52 g).

Provenance & Evidence