Diethylamine → 4-(Diethylamino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

4-Bromobenzonitrile (2.000 g, 10.99 mmol), diethylamine (3.41 mL, 32.96 mmol) and POTASSIUM CARBONATE (4.56 g, 32.96 mmol) were mixed in dry acetonitrile (10 mL) under argon in a microwave vial. The vial was sealed and heated with microvawes for 60 minutes at 160°C. Added diethylamine (3.41 mL, 32.96 mmol) and heated at 160°C for 3 hours. Added Palladium(II) acetate (0.123 g, 0.55 mmol) and 2-(Dicyclohexylphosphino)-2',4',6'-tri-i- propyl-1,1'-biphenyl (0.524 g, 1.10 mmol), purged with argon for 5 minutes and heated in an oil bath at 100°C for 24 hours. The reaction was cooled to rt and partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (40 mL). The layers were separated and the aqueous phase extracted with EtOAc (100 mL). The organics were combined, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel gave 4-(diethylamino)benzonitrile (0.750 g, 39.2 %)

Provenance & Evidence