2-Chloroaniline → HCID 22148450, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromobenzonitrile (3.0 g, 16.4 mmol) in toluene (40 mL) is added 2-chloroaniline (2.09 mL, 19.7 mmol), cesium carbonate (7.5 g, 23.0 mmol), palladium (II) acetate (110 mg, 0.50 mmol) and S-BINAP (460 mg, 0.74 mmol). The reaction mixture is then heated to 100° C. for 12 hours under an argon atmosphere. Once complete, the reaction is cooled to room temperature, diluted with diethyl ether and filtered. The filtrate is then concentrated and purified by column chromatography (6% ethyl acetate in hexanes) to afford 1.35 g of 4-[(2-chlorophenyl)amino]benzonitrile.

Provenance & Evidence