Reacción #67426

Ecuación de reacción

6-chloromethyl-4-fluoro-benzo[1,3]dioxole

NaCN

water

→

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

Rendimiento 70.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with EtOAc (50 mL×3)
2. 2
   LavadoThe combined organic layers were washed with water (50 mL) and brine (50 mL)
3. 3
   Secadodried over Na2SO4
4. 4
   Otroevaporated under reduced pressure
5. 5
   Otroto give the crude product, which
6. 6
   Otrowas purified by column chromatography on silica gel (petroleum ether/E.A.=10/1)

Procedimiento

A mixture of 6-chloromethyl-4-fluoro-benzo[1,3]dioxole (0.80 g, 4.3 mmol) and NaCN (417 mg, 8.51 mmol) in DMSO (20 mL) was stirred at 30° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/E.A.=10/1) to afford 2-(7-fluorobenzo[d][1,3]dioxol-5-yl)acetonitrile (530 mg, 70%). 1H NMR (300 MHz, CDCl3) 6.68-6.64 (m, 2H), 6.05 (s, 2H), 3.65 (s, 2H). 13C-NMR δ151.1, 146.2, 134.1, 124.2, 117.5, 110.4, 104.8, 102.8, 23.3.

Fuente