Benzonitrile → HCID 178418369, compound

Participants

Reaction Steps

As outlined in Scheme 9, benzonitrile is treated with sodium azide and zinc chloride to give 5-phenyltetrazole 22 which is convened to the N-trityl derivative 23 by treatment with triphenylmethyl chloride and triethylamine. The zinc reagent 24 was prepared by treatment with n-butyl lithium followed by zinc chloride. Coupling with 4-iodotoluene using the catalyst bis(triphenylphosphine)nickel(II) dichloride gives the biphenyl product 25 in high yield. Treatment with N-bromosuccmimide in refluxing carbon tetrachloride in the presence of a radical initiator such as benzoyl peroxide or 2,2'-azobisisobutyronitrile (AIBN) gives bromide 26.

Provenance & Evidence