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

HRID 2406957Notes

Reaction equation

HRID 2406957 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

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

Product 1

HCID 155411804-(4-Trifluoromethylphenyl)phenolYield 55%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

4-(trifluoromethyl)phenylboronic acid (263 mg, 1.39 mmol) was suspended in water (2 mL). 4-bromophenol (0.200 g, 1.16 mmol), potassium carbonate (484 mg, 3.47 mmol), and palladium(II) acetate (13.3 mg, 0.0580 mmol) were added. The reaction was allowed to stir open to ambient atmosphere for 60 hours. The reaction was filtered through Celite and extracted three times with ethyl acetate. The combined organics were washed with 1N HCl, water, and brine, dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography (0-20% ethyl acetate in heptanes) gave 4′-(trifluoromethyl) biphenyl-4-ol (150 mg, 55%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 7.63-7.70 (m, 4H), 7.50-7.54 (m, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.81 (s, 1H). MS (M-1): 237.0.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organics were washed with 1N HCl, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (0-20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-e5ba4a47a53b488296ad6b86c45e1d51
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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