Sodium Carbonate → 2-Cyano-4'-methylbiphenyl

HRID 369647Notes

Reaction equation

HRID 369647 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.C(=O)([O-])[O-].[Na+].[Na+].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.C(O)COCCOCCO.O.CS(C)=O.[Pd](Cl)Cl.C([O-])(=O)C.[Na+]>[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

11

Reactant 4

HCID 10340Sodium CarbonateHCID 133912-ChlorobenzonitrileHCID 79799Tolylboronic acidHCID 53487040Sodium 3,3',3''-phosphinetriyltribenzenesulfonate hydrate

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 82.7%

Reagents, catalysts & solvents 6

HCID 24290Palladium ChlorideCatalystHCID 517045Sodium AcetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 7809P-XyleneSolventHCID 8172Triethylene GlycolSolvent

Procedure

15 g of 2-chlorobenzonitrile, 14.8 g of p-tolueneboronic acid and 28.9 g of sodium carbonate in 50 ml of p-xylene, 40 ml of triethylene glycol and 10 ml of water were heated to 120° C. At 80° C., a mixture of 19.3 mg of palladium chloride, 17.9 mg of sodium 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 17.4 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-2a4453f476f1430bb11f1c761e5969a1
Source dataset
uspto-grants-2000_10
Patent number
US06140265

Reaction notes

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