4-Fluorophenol → 2-(4-Fluorophenoxy)pentan-3-one

HRID 445885Notes

Reaction equation

HRID 445885 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([C:18](=[O:21])[CH2:19][CH3:20])[CH3:17]>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:16]([C:18](=[O:21])[CH2:19][CH3:20])[CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 5450922-Bromo-3-pentanone

Product 1

HCID 585666502-(4-Fluorophenoxy)pentan-3-oneYield 40.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluorophenol (8.0 g, 71.4 mmol) in dimethylformamide (130.0 mL) was added potassium carbonate (13.5 g, 97.4 mmol) and 2-bromopentan-3-one (836) (10.7 g, 64.9 mmol). The suspension was heated at 70° C. for 18 h, cooled to room temperature, diluted with water (50 mL), and extracted with ethyl acetate (2×25 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (0-20% EtOAc in hexanes) to provide the desired 2-(4-fluorophenoxy)pentan-3-one (837) (5.2 g, 40.8%) as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3595f97a59c749a7a420bba8a8d49628
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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