Reacción #669145

Ecuación de reacción

4-acetyl-2-nitroaniline

1,3-dibromobenzene

potassium carbonate

→

N-(3-bromophenyl)-4-acetyl-2-nitroaniline

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Otrothe solid reaction cake
3. 3
   Extracciónis extracted with a mixture of dichloromethane and methanol (9:1)
4. 4
   ConcentraciónThe extract is concentrated under reduced pressure
5. 5
   ExtracciónThe residue is extracted with ethyl acetate
6. 6
   ConcentraciónThis extract is concentrated under reduced pressure
7. 7
   Lavadothe residue is eluted through silica gel with a mixture of petroleum ether and ethyl acetate (4:1)
8. 8
   Otroto afford the pure product

Procedimiento

A mixture of 4-acetyl-2-nitroaniline (3.41 g, 18.94 mmol), 1,3-dibromobenzene (4.6 ml, 38.06 mmol), potassium carbonate (2.62 g, 19 mmol) and a catalytic amount of copper bronze is heated with stirring to 180° C. under a stream of nitrogen for 2 days. After cooling the solid reaction cake is extracted with a mixture of dichloromethane and methanol (9:1). The extract is concentrated under reduced pressure. The residue is extracted with ethyl acetate. This extract is concentrated under reduced pressure and the residue is eluted through silica gel with a mixture of petroleum ether and ethyl acetate (4:1) to afford the pure product. Yield 0.67 g (10.6%). M.p. 142-144° C.

Fuente