Reacción #46179

Ecuación de reacción

Thionyl chloride

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

→

5-chloromethyl-2,2-difluoro-benzo[1,3]dioxole

Rendimiento 56.1%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated to dryness
2. 2
   OtroThe residue was partitioned between an aqueous solution of saturated sodium bicarbonate (100 mL) and dichloromethane (100 mL)
3. 3
   ExtracciónThe separated aqueous layer was extracted with dichloromethane (150 mL)
4. 4
   Secadothe organic layer was dried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated to dryness

Procedimiento

Thionyl chloride (45 g, 38 mmol) was slowly added to a solution of (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 38 mmol) in dichloromethane (200 mL) at 0° C. The resulting mixture was stirred overnight at room temperature and then evaporated to dryness. The residue was partitioned between an aqueous solution of saturated sodium bicarbonate (100 mL) and dichloromethane (100 mL). The separated aqueous layer was extracted with dichloromethane (150 mL) and the organic layer was dried over sodium sulfate, filtered, and evaporated to dryness to give crude 5-chloromethyl-2,2-difluoro-benzo[1,3]dioxole (4.4 g) which was used directly in the next step.

Fuente