Reacción #710497

Ecuación de reacción

EtOAc

Trimethylsilylcyanid

4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine

Tetra-n-butylammoniumfluoride

→

[4-chloro-6-(trifluoromethyl)pyridin-3-yl]acetonitrile

Rendimiento 65.1%

Disolventes

—

petroleum ether

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas consumed
2. 2
   ConcentraciónThe mixture was concentrated
3. 3
   Otrothe residue was purified by silica gel chromatography
4. 4
   Lavadoeluted with petroleum ether

Procedimiento

Trimethylsilylcyanid (TMSCN) (69.3 g, 0.7 mol) was added to a solution of 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13) (80 g, 0.348 mol) and Tetra-n-butylammoniumfluoride (129.5 g, 0.7 mol) in acetonitrile (1.5 L) slowly. Then the mixture was stirred at 20-30° C. for 2 hours. Thin layer chromatography (petroleum ether: EtOAc=3:1) showed all of starting material was consumed. The mixture was concentrated and the residue was purified by silica gel chromatography eluted with petroleum ether: EtOAc=20:1˜3:1 to yield [4-chloro-6-(trifluoromethyl)pyridin-3-yl]acetonitrile (Int-14) (50 g, 60% from NMR, 39% of yield) as yellow syrup.

Fuente