Carbon Dioxide → 4-Cyano-2-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-methyl-benzonitrile (10.008 g, 51.05 mmol) (commercially available) in tetrahydrofuran (“THF”) (350 ml) was added n-butyl lithium (1.6M in THF) (35 ml, 56.16 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 1 hour. Then carbon dioxide (24.933 g, 566.66 mmol) was added. The reaction mixture was allowed to warm to ambient temperature. The reaction mixture was quenched by addition of water (300 ml), and extracted with diethyl ether (3×300 ml). The phases were separated. The aqueous phase was acidified by addition of aqueous hydrochloric acid (concentrated) and extracted with chloroform (3×200 ml). The combined organic phases were concentrated and used without further purification.

Provenance & Evidence