2-Chlorobenzonitrile → 2-Cyano-4'-methylbiphenyl

HRID 636904Notes

Reaction equation

HRID 636904 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>[Ni]>[CH3:4][C:3]1[CH:6]=[CH:7][C:8]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:9][CH:2]=1

Participants

3

Reactant 1

HCID 133912-Chlorobenzonitrile

Product 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In one practical embodiment, 4-methylphenylchloride in tetrahydrofuran solvent is reacted with magnesium to form 4-methylphenylmagnesium chloride. An equivalent of zinc chloride is added to this mixture to form 4-methylphenylzinc chloride. This mixture is then combined with the 2-chlorobenzonitrile and the nickel catalyst components and reacted to form the 2-(4′-methylphenyl)benzonitrile.

Sources & evidence

ORD record
ord-8efb42094423480d8dacd3be8b5a4e4e
Source dataset
uspto-grants-2001_02
Patent number
US06194599B1

Reaction notes

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