Phenylboronic Acid → 4-Methoxybiphenyl

HRID 1247707Notes

Reaction equation

HRID 1247707 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=O)=O.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F-].[K+]>C1(C2(C3C=CC=CC=3)CC2(P(C(C)(C)C)C(C)(C)C)C)C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 5793374-Methoxyphenyl trifluoromethanesulfonate

Product 1

HCID 119434-MethoxybiphenylYield 97.1%

Reagents, catalysts & solvents 2

HCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphaneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, 4-trifluoromethane-sulfonyloxyanisole (0.49 g, 1.9 mmol), phenylboronic acid (0.29 g, 2.4 mmol), potassium fluoride (0.24 g, 4.2 mmol), (π-allyl)palladium chloride (3.6 mg, 0.01 mmol), 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.0 mg, 0.04 mmol) obtained in Example 4 and toluene (4 ml) were placed in a reaction flask and stirred for 1.5 hours at 80° C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give the title compound (0.34 g, 96%) as white crystal.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed under reduced pressure
  5. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-e3fb41bd2fad4df8a86c663d5849125d
Source dataset
uspto-grants-2006_10
Patent number
US07129367B2

Reaction notes

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