Reacción #1563921

Ecuación de reacción

4-fluorophenol

2-bromo-1,1-dimethoxyethane

K2CO3

→

title compound

Rendimiento 60.0%

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

Rendimiento 60.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaHeat the solution
2. 2
   Temperaturato reflux
3. 3
   FiltraciónFilter the mixture
4. 4
   Concentraciónconcentrate the filtrate under reduced pressure
5. 5
   Lavadoeluting with a gradient of 0% to 50% EtOAc/hexanes
6. 6
   ConcentraciónConcentrate the fractions
7. 7
   workup.ADDITIONcontaining the desired product under reduced pressure

Procedimiento

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)+.

Fuente