Reaction #1563921

Reaction equation

4-fluorophenol

2-bromo-1,1-dimethoxyethane

K2CO3

→

title compound

Yield 60.0%

1-(2,2-dimethoxyethoxy)-4-fluorobenzene

Yield 60.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureHeat the solution
2. 2
   Temperatureto reflux
3. 3
   FiltrationFilter the mixture
4. 4
   Concentrationconcentrate the filtrate under reduced pressure
5. 5
   Washeluting with a gradient of 0% to 50% EtOAc/hexanes
6. 6
   ConcentrationConcentrate the fractions
7. 7
   workup.ADDITIONcontaining the desired product under reduced pressure

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)+.

Source