Benzonitrile → HCID 178418369, compound

HRID 481759Notes

Reaction equation

HRID 481759 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5](#[N:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[Cl-].[Zn+2].[Cl-]>[C:6]1([C:5]2[NH:12][N:3]=[N:2][N:1]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 33557Sodium Azide

Product 1

HCID 178418369HCID 178418369, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

As outlined in Scheme 8, benzonitrile is treated with sodium azide and zinc chloride to give 5-phenyltetrazole 14 which is converted to the N-trityl derivative 15 by treatment with triphenylmethyl chloride and triethylamine. The zinc reagent 16 was prepared by treatment with n-butyllithium followed by zinc chloride. Coupling with 4-iodotoluene using the catalyst bis(triphenylphosphine)nickel(II) dichloride gives the biphenyl product 17 in high yield. Treatment with N-bromosuccinimide in refluxing carbon tetrachloride, in the presence of a radical initiator such as benzoyl peroxide or 2,2'-azobisisobutyronitrile (AIBN), gives bromide 18.

Sources & evidence

ORD record
ord-8eca110288f744d997266c172ef3d46e
Source dataset
uspto-grants-1998_08
Patent number
US05789587

Reaction notes

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