Pyridine → 4-Cyano-2,6-dimethylphenyl trifluoromethanesulfonate

HRID 2426747Notes

Reaction equation

HRID 2426747 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[C:24]([CH3:25])=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[CH3:26].N1C=CC=CC=1>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[CH3:26])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 574225934-Cyano-2,6-dimethylphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-1ff1fbde5a84470f8815b24b8080fa0a
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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