3-Hydroxybenzyl alcohol → [3-(4-Fluorophenoxy)phenyl]methanol

HRID 1678580Notes

Reaction equation

HRID 1678580 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Br[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].N1C2C(=CC=CC=2O)C=CC=1>CN1CCN(C)C1=O.O>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 19238-HydroxyquinolineHCID 99931-Bromo-4-fluorobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 10584901[3-(4-Fluorophenoxy)phenyl]methanolYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
150 °C

Procedure

3-Hydroxybenzyl alcohol (3.0 g, 24.6 mmol) was dissolved in 1,3-dimethyl-2-imidazolidinone (50 mL). 4-Bromofluorobenzene (6.5 g, 36.9 mmol), potassium carbonate (2.0 g, 14.8 mmol), 8-quinolinol (71 mg, 0.5 mmol), and copper chloride(I) (49 mg, 0.5 mmol) were added thereto, and then the mixture was stirred at 150° C. for 2 days. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=90:10 to 80:20) to give the title compound (0.98 mg, yield 18%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=90:10 to 80:20)

Sources & evidence

ORD record
ord-45e40532b07d4302beef479dedc63643
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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