2-Chlorobenzonitrile → Zinc

Participants

Reaction Steps

Preparation of 2,2′-dicyanobiphenyl by nickel catalyzed reaction of 2-cyanophenylzinc bromide with 2-chlorobenzonitrile: Activated zinc was prepared and reacted with 2-bromobenzonitrile to provide 2-cyanophenylzinc bromide, as follows: A mixture of 0.208 g (30.0 mmol) lithium wire and 3.91 g (30.5 mmol) naphthalene in 15 mL of THF was stirred at room temperature for 4 h. To the resultant dark green solution was then added a solution of 2.04 g (15.0 mmol) zinc chloride in 15 mL of THF. After stirring the mixture for 10 minutes, 0.91 g (5.0 mmol) 2-bromobenzonitrile was added and the reaction mixture refluxed for 8 h. The resultant mixture was then filtered through a small pad of celite under nitrogen to provide a clear, dark solution of 2-cyanophenylzinc bromide.

Provenance & Evidence