Benzonitrile → Tritylamine

Participants

Reaction Steps

Cerium chloride heptahydrate (15.0 g, 40 mmol) was dried and stirred with 80 mL of dry tetrahydrofuran as described in Example 1. To this was added by cannulation below -50° a solution of phenyllithium prepared by addition of 16 mL of 2.5M n-butyllithium in hexanes (40 mmol) to 6.28 g (40 mmol) of bromobenzene in 15 mL of tetrahydrofuran below -40°. The mixture was stirred in a dry ice-acetone bath for 30 minutes, and 1.34 g (13 mmol) of benzonitrile in 2 mL of tetrahydrofuran were added. The bath was removed and the mixture was stirred for 2 hours. Isolation as described in Example 1 gave 3.30 g (98%) of triphenylmethylamine, identical by infrared, 1H and 13C NMR spectroscopy with an authentic sample.

Provenance & Evidence