Potassium Cyanide → 2,2-Difluoro-1,3-benzodioxole-5-acetonitrile

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Reaction Steps

To a solution of 2,2-difluoro-5-bromomethyl-1,3-benzodioxole (41.0 g) in absolute alcohol (160 ml) at 60° to 70° C a hot solution of potassium cyanide (22.1 g, 0.34 mole) in water (30 ml) is added. There is a slight exotherm and within 5 minutes potassium bromide separates out of the reaction mixture. The reaction mixture is refluxed for 1.5 hours, cooled and added to ice-water. The mixture is extracted with ether (3×100 ml), the combined extracts are washed with water (2×50 ml), dried over sodium sulfate and evaporated to afford a dark oil. Vacuum distillation yields 21.2 g of title product; b.p. 64° to 67° C (at 0.03 mm); i.r. (neat) 2255 cm-1 ; nmr (CCl4) δ 3.68 (S, 2H), 7.00 (S, 3H).

Provenance & Evidence