Potassium Phosphate, Tribasic → 3'-Formyl-2,6-dimethylbiphenyl-4-carbonitrile

HRID 2426748Notes

Reaction equation

HRID 2426748 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:8]=1[CH3:16])(=O)=O.[CH:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)=[O:20].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:19]([C:21]1[CH:26]=[C:25]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:8]=2[CH3:16])[CH:24]=[CH:23][CH:22]=1)=[O:20]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27343563-Formylphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 574225934-Cyano-2,6-dimethylphenyl trifluoromethanesulfonate

Product 1

HCID 866328313'-Formyl-2,6-dimethylbiphenyl-4-carbonitrile

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Trifluoromethanesulfonic anhydride was dropwise added, under ice-cooling, to a mixture of 4-hydroxy-3,5-dimethylbenzonitrile, pyridine and dichloromethane, followed by stirring at room temperature for 2 hours to obtain 4-cyano-2,6-dimethylphenyl trifluoromethanesulfonate. In an atmosphere of nitrogen, a mixture of 4-cyano-2,6-dimethylphenyl trifluoromethanesulfonate, (3-formylphenyl)boronic acid, palladium acetate, dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tripotassium phosphate, toluene and water was stirred at room temperature for 6 hours to obtain 3′-formyl-2,6-dimethylbiphenyl-4-carbonitrile.

Sources & evidence

ORD record
ord-2bdb7b7634bd48f892ea5d4a10be53ba
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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