4-Fluorophenol → HCID 59346670, compound

HRID 1476739Notes

Reaction equation

HRID 1476739 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:13][O:12][CH:11]([O:14][CH3:15])[CH2:10][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 59346670HCID 59346670, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 4-fluorophenol (5.5 g, 49.1 mmol) in acetonitrile (49 mL) and treat the solution with 2-bromo-1,1-dimethoxyethane (11.6 mL, 98.1 mmol) and K2CO3 (16.95 g, 122.7 mmol). Heat the solution to reflux with stirring for five days. Filter the mixture, and concentrate the filtrate under reduced pressure. Subject the resulting crude material to silica gel chromatography eluting with a gradient of 0% to 50% EtOAc/hexanes. Concentrate the fractions containing the desired product under reduced pressure to furnish the title compound as a colorless oil (5.85 g, 60% yield). Mass spectrum (m/z) 218 (M+NH4)+, 223 (M+Na)+.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux
  3. filtrationFilter the mixture
  4. concentrationconcentrate the filtrate under reduced pressure
  5. washeluting with a gradient of 0% to 50% EtOAc/hexanes
  6. concentrationConcentrate the fractions
  7. additioncontaining the desired product under reduced pressure

Sources & evidence

ORD record
ord-b0745f92450247238ec72e8e948c144c
Source dataset
uspto-grants-2016_08
Patent number
US09402838B2

Reaction notes

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