4-Bromophenol → 4-(4-Trifluoromethylphenyl)phenol

HRID 1914273Notes

Reaction equation

HRID 1914273 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 155411804-(4-Trifluoromethylphenyl)phenolYield 87.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

4-Bromophenol (5 g, 28.9 mmol), 4-trifluoromethyl phenyl boronic acid (6.59 g, 34.7 mmol), potassium carbonate (12 g, 86.7 mmol) and palladium acetate (0.324 g, 1.445 mmol) are placed in water (50 mL), and the resulting mixture is stirred at room temperature over night under open air. The mixture is filtered through celite and extracted with ethyl acetate (3×200 ml). The combined organic layers are washed with water, 1N HCl, water, brine, dried (MgSO4), concentrated and chromatographed to yield the title compound as a white solid (6.0 g, 87%).

Workup

  1. filtrationThe mixture is filtered through celite
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organic layers are washed with water, 1N HCl, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-67e7b8abcd0a49779b99767993fbc83d
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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