Reacción #46220

Ecuación de reacción

6-chloromethyl-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine

NaCN

→

(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile

Rendimiento 94.5%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was poured into ice
2. 2
   Extracciónextracted with EtOAc (50 mL×3)
3. 3
   SecadoThe combined organic layers were dried over anhydrous Na2SO4
4. 4
   Otroevaporated
5. 5
   Otroto give a crude product, which
6. 6
   Otrowas purified by silica gel column (Petroleum Ether/EtOAc 10:1)

Procedimiento

A mixture of 6-chloromethyl-2,2,4,4-tetrafluoro-4H-benzo[1,3]dioxine (6.2 g) and NaCN (2.07 g, 42.3 mmol) in DMSO (50 mL) was stirred at room temperature for 2 h. The reaction mixture was poured into ice and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to give a crude product, which was purified by silica gel column (Petroleum Ether/EtOAc 10:1) to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile (4.5 g, 68% over 3 steps). 1H NMR (CDCl3, 300 MHz) δ 7.57-7.60 (m, 2H), 7.20 (d, J=8.7 Hz, 1H), 3.82 (s, 2H).

Fuente