Reaction #67724

Reaction equation

Sodium hydroxide

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

benzyltriethylammonium

chloride

1-bromo-2-chloroethane

→

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

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   DryingThe combined organic layers were dried over sodium sulfate
3. 3
   Otherevaporated to dryness

Procedure

Sodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[1,3]dioxol-5-yl-acetonitrile, benzyltriethylammonium, chloride (3.00 g, 15.3 mmol), and 1-bromo-2-chloroethane (4.9 g, 38 mmol) at 70° C. The mixture was stirred overnight at 70° C. before the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude 1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonitrile, which was used directly in the next step.

Source