Potassium Phosphate, Tribasic → Methyl 4'-(3-fluoro-3-methylbutoxy)-2,2'-dimethylbiphenyl-3-carboxylate
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]([F:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH3:15].[CH3:16][C:17]1[C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[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>[F:14][C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH3:16])=[C:3]([CH3:15])[CH:4]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
In an atmosphere of nitrogen, a mixture of 1-bromo-4-(3-fluoro-3-methylbutoxy)-2-methylbenzene, methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, palladium acetate, dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tripotassium phosphate, toluene and water was stirred at 80° C. for 12 hours to obtain methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate. Lithium aluminum hydride was added to a THF solution of the resulting methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate under ice-cooling, followed by warming up to room temperature and stirring for 1 hour to obtain [4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-yl]methanol.
Sources & evidence
- ORD record
- ord-bcc13e645c68438194e78de699a1f9d1
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968552B2
Reaction notes
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