Reacción #66119

Ecuación de reacción

p-nitro-phenol

potassium carbonate

1,2-dibromoethane

→

1-(2-bromo-ethoxy)-4-nitro-benzene

Rendimiento 70.7%

Disolventes

butanone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 18 h
3. 3
   TemperaturaThe mixture was cooled
4. 4
   Filtraciónthe inorganic salts filtered
5. 5
   Concentraciónthe filtrate concentrated under vacuum
6. 6
   Otroto give a brown viscous liquid, which
7. 7
   Otrowas partitioned between dichloromethane and water
8. 8
   OtroThe organic phase was separated
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otroto obtain a residue which
11. 11
    Otrowas purified by column chromatography

Procedimiento

A mixture of p-nitro-phenol (6.0 g, 43.1 mmol), potassium carbonate (14.9 g, 108 mmol) and 1,2-dibromoethane (24.3 g, 129 mmol) in butanone (80 mL) was heated at reflux for 18 h. The mixture was cooled, the inorganic salts filtered and the filtrate concentrated under vacuum to give a brown viscous liquid, which was partitioned between dichloromethane and water. The organic phase was separated and concentrated in vacuo to obtain a residue which was purified by column chromatography using 4% ethyl acetate in petroleum ether as eluent to afford 1-(2-bromo-ethoxy)-4-nitro-benzene (7.5 g, 70%) as a light yellow solid.

Fuente