Reacción #67421

Ecuación de reacción

4-chloro-6-(chloromethyl)benzo[d][1,3]dioxole

NaCN

water

→

2-(7-chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile

Rendimiento 59.9%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with EtOAc (30 mL×3)
2. 2
   LavadoThe combined organic layers were washed with water and brine
3. 3
   Secadodried over Na2SO4
4. 4
   Otroevaporated under reduced pressure

Procedimiento

A mixture of 4-chloro-6-(chloromethyl)benzo[d][1,3]dioxole (6.0 g, 29 mmol) and NaCN (1.6 g, 32 mmol) in DMSO (20 mL) was stirred at 40° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure to afford 2-(7-chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile (3.4 g, 58%). 1H NMR δ 6.81 (s, 1H), 6.71 (s, 1H), 6.07 (s, 2H), 3.64 (s, 2H). 13C-NMR δ149.2, 144.3, 124.4, 122.0, 117.4, 114.3, 107.0, 102.3, 23.1.

Fuente