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

HRID 369627Notes

Reaction equation

HRID 369627 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1([CH3:19])[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.[F-].[K+].C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].O>CC1C=CC(C)=CC=1.OCC(CO)O.O.CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=1)#[N:5]

Participants

10

Reactant 4

HCID 133912-ChlorobenzonitrileHCID 79799Tolylboronic acidHCID 522689Potassium FluorideHCID 53487040Sodium 3,3',3''-phosphinetriyltribenzenesulfonate hydrate

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 86.4%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 753GlycerolSolventHCID 962WaterSolventHCID 7809P-XyleneSolvent

Procedure

15 g of 2-chlorobenzonitrile, 15.8 g of p-tolueneboronic acid and 15.8 g of potassium fluoride in 50 ml of p-xylene, 40 ml of glycerol and 10 ml of water were heated to 120° C. At 80° C., a mixture of 24.7 mg of palladium acetate and 0.55 ml of TPPTS/H2O solution (0.6 molar) in 2.5 ml of DMSO was added. After the reaction was complete, the phases were separated. The aqueous phase was washed with 50 ml of toluene. The combined organic phases were washed with 20 ml of water and subsequently dried over sodium sulfate. Crystallization from n-heptane gave 18.2 g of 2-cyano-4'-methylbiphenyl.

Workup

  1. additionwas added
  2. customthe phases were separated
  3. washThe aqueous phase was washed with 50 ml of toluene
  4. washThe combined organic phases were washed with 20 ml of water
  5. dry with materialsubsequently dried over sodium sulfate
  6. customCrystallization from n-heptane

Sources & evidence

ORD record
ord-9663dec4e0784817bf060005278388b6
Source dataset
uspto-grants-2000_10
Patent number
US06140265

Reaction notes

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