Potassium Phosphate, Tribasic → Methyl 4'-hydroxy-2,2',6'-trimethylbiphenyl-3-carboxylate

HRID 2426749Notes

Reaction equation

HRID 2426749 reaction equation
[CH3:1][C:2]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([OH:29])=[CH:24][C:23]=1[CH3:30].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>[OH:29][C:25]1[CH:26]=[C:27]([CH3:28])[C:22]([C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[CH3:1])=[C:23]([CH3:30])[CH:24]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 819704-Bromo-3,5-dimethylphenolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57422592Methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 57787600Methyl 4'-hydroxy-2,2',6'-trimethylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In an atmosphere of nitrogen, a mixture of methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 4-bromo-3,5-dimethylphenol, palladium acetate, dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tripotassium phosphate, toluene and water was stirred for 14.5 hours with heating at 60° C. to obtain methyl 4′-hydroxy-2,2′,6′-trimethylbiphenyl-3-carboxylate.

Sources & evidence

ORD record
ord-4b9230ad3ec74be0a8c4abb1ed5496be
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

Loading…