2-Chlorobenzonitrile → Zinc

HRID 636905Notes

Reaction equation

HRID 636905 reaction equation
C(C1C=CC=CC=1C1C=CC=CC=1C#N)#N.[Br-].[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Zn+:26])#[N:19].ClC1C=CC=CC=1C#N.[Br:36]C1C=CC=CC=1C#N>[Ni]>[Zn:26].[Br-:36].[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Zn+:26])#[N:19]

Participants

7

Reactant 4

HCID 133912-ChlorobenzonitrileHCID 162722-BromobenzonitrileHCID 266827[1,1'-Biphenyl]-2,2'-dicarbonitrileHCID 178509677HCID 178509677, compound

Product 2

HCID 23994ZincHCID 178509677HCID 178509677, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

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.

Sources & evidence

ORD record
ord-13e2ce49140d41d98264132cb70707a4
Source dataset
uspto-grants-2001_02
Patent number
US06194599B1

Reaction notes

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