4-Chlorobenzonitrile → (1,1'-Biphenyl)-4-carbonitrile, 4'-methyl-

HRID 467242Notes

Reaction equation

HRID 467242 reaction equation
[Na].Cl[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[O-2].[Ca+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([C:3]2[CH:10]=[CH:9][C:6]([CH3:7])=[CH:5][CH:4]=2)=[CH:4][CH:5]=1)#[N:8]

Participants

7

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 5360545SodiumHCID 6850728Calciumoxide

Product 1

HCID 170889(1,1'-Biphenyl)-4-carbonitrile, 4'-methyl-Yield 49%

Reagents, catalysts & solvents 3

HCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3.56 g (20 mmol) of sodium p-tolunesulfinate, 2.75 g (20 mmol) of p-chlorobenzonitrile, 0.0225 g (0.1 mmol) of palladium acetate, 0.0478 g (0.12 mmol) of 1,2-bis(diphenylphosphino) ethane, 11.2 g (200 mmol) of calcium oxide and 60 ml of N-methyl-2-pyrrolidone were placed in a 100 ml round bottom flask and reacted at 150° C. in a nitrogen gas stream for 6 hours. After the completion of the reaction, the reaction mixture solution was analyzed by means of high performance liquid chromatography. The analysis showed that 4.9 mmol (yield 25%) of 4'-cyano-4-methyl-biphenyl was formed in the reaction mixture solution.

Workup

  1. customreacted at 150° C. in a nitrogen gas stream for 6 hours
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-f6e92040a2934cdd8f97da5246c2a4cd
Source dataset
uspto-grants-1992_10
Patent number
US05159082

Reaction notes

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