Reacción #1447099

Ecuación de reacción

hydrochloric acid

Tert-butyl nitrite

4-bromo-2-(4-ethyl-benzyl)-5-methoxy-phenylamine

CuCN

→

title compound

4-Bromo-2-(4-ethyl-benzyl)-5-methoxy-benzonitrile

Disolventes

DMSO

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   ExtracciónThe resulting mixture is extracted with ethyl acetate
3. 3
   Secadothe combined extracts are dried (Na2SO4)
4. 4
   OtroAfter removal of the solvent
5. 5
   Otrothe residue is purified by chromatography on silica gel (cyclohexane/dichloromethane 3:1->1:3)

Procedimiento

Tert-butyl nitrite (1.1 mL) is added to a 60° C.-warm solution of CuCN (0.36 g) in DMSO (3 mL). Then, a solution of 4-bromo-2-(4-ethyl-benzyl)-5-methoxy-phenylamine (1.0 g) in DMSO is added dropwise and the resulting solution is stirred for 1 h at 60° C. After cooling to room temperature, the solution is acidified by the addition of 5 N aqueous hydrochloric acid. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4). After removal of the solvent, the residue is purified by chromatography on silica gel (cyclohexane/dichloromethane 3:1->1:3) to give the title compound.

Fuente