Reaktion #1447099

Reaktionsgleichung

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

Lösungsmittel

DMSO

DMSO

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle