4-Fluorophenol → HCID 59346670, compound

HRID 1854225Notes

Reaction equation

HRID 1854225 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-f2d42d3d26bb4c69a52c7844a0cddf00
Source dataset
uspto-grants-2015_02
Patent number
US08962659B2

Reaction notes

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