Water → 4-Methoxybiphenyl

HRID 1837800Notes

Reaction equation

HRID 1837800 reaction equation
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C12(PC34CC5CC(CC(C5)C3)C4)CC3CC(CC(C3)C1)C2.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].O.Cl[C:52]1[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:59][O:58][C:55]1[CH:56]=[CH:57][C:52]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:53][CH:54]=1

Participants

8

Reactant 5

HCID 962WaterHCID 121674-ChloroanisoleHCID 61695Pentapotassium TriphosphateHCID 78412Phenyl dihydrogen orthoborateHCID 11077518Di-1-adamantylphosphine

Product 1

HCID 119434-MethoxybiphenylYield 84%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Phenylboric acid (366 mg, 3.0 mmols), palladium acetate (4.49 mg, 0.02 mmols), diadamantyl phosphine (12.1 mg, 0.04 mmols) and potassium triphosphate (1.273 g, 6 mmols) are placed in 6 ml of dioxane and water (0.18 ml, 10 mmols) under argon. The reaction mixture is heated in an oil bath of 100° C. and stirred for 5 minutes. Afterwards, 4-chloroanisole (0.27 ml, 2 mmols) is added. The reaction mixture is then stirred for 18 hours at 100° C. and subsequently cooled. The title compound is purified by flash chromatography over silica gel. The yield is 84%.

Workup

  1. stirringThe reaction mixture is then stirred for 18 hours at 100° C.
  2. temperaturesubsequently cooled
  3. customThe title compound is purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-e0f964c6f2964f8ebb304d8208e26c66
Source dataset
uspto-grants-2004_08
Patent number
US06784295B2

Reaction notes

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