Reaction #67723

Reaction equation

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

sodium cyanide

→

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

Yield 78.6%

Solvents

dimethylsulfoxide

Conditions

Workup

1. 1
   workup.ADDITIONThe reaction mixture was poured into ice
2. 2
   Extractionextracted with ethyl acetate (300 mL)
3. 3
   DryingThe organic layer was dried over sodium sulfate
4. 4
   Otherevaporated to dryness

Procedure

A mixture of crude 5-chloromethyl-2,2-difluoro-benzo[1,3]dioxole (4.4 g) and sodium cyanide (1.36 g, 27.8 mmol) in dimethylsulfoxide (50 mL) was stirred at room temperature overnight. The reaction mixture was poured into ice and extracted with ethyl acetate (300 mL). The organic layer was dried over sodium sulfate and evaporated to dryness to give crude (2,2-difluoro-benzo[1,3]dioxol-5-yl)-acetonitrile (3.3 g) which was used directly in the next step.

Source