Reaktion #1563921

Reaktionsgleichung

4-fluorophenol

2-bromo-1,1-dimethoxyethane

K2CO3

→

title compound

Ausbeute 60.0%

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

Ausbeute 60.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturHeat the solution
2. 2
   Temperaturto reflux
3. 3
   FiltrationFilter the mixture
4. 4
   Einengenconcentrate the filtrate under reduced pressure
5. 5
   Wascheneluting with a gradient of 0% to 50% EtOAc/hexanes
6. 6
   EinengenConcentrate the fractions
7. 7
   workup.ADDITIONcontaining the desired product under reduced pressure

Vorschrift

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)+.

Quelle