Naphthalene → HCID 178509677, compound

HRID 636906Notes

Reaction equation

HRID 636906 reaction equation
[Li].C1C2C(=CC=CC=2)C=CC=1.[Cl-].[Zn+2:13].[Cl-].[Br:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>C1COCC1>[Br-:15].[C:18]([C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[Zn+:13])#[N:19]

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 162722-BromobenzonitrileHCID 3007855ZincchlorideHCID 3028194Lithium

Product 1

HCID 178509677HCID 178509677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. stirringAfter stirring the mixture for 10 minutes
  2. temperaturethe reaction mixture refluxed for 8 h
  3. filtrationThe resultant mixture was then filtered through a small pad of celite under nitrogen

Sources & evidence

ORD record
ord-a89b9d9bd3544b388857e17af3b9b42f
Source dataset
uspto-grants-2001_02
Patent number
US06194599B1

Reaction notes

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