Water → 3-Phenyl-2,1-benzisoxazole-5-acetonitrile

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Reaction Steps

A mixture of 9.1 g (0.032 mole) of 5-(bromomethyl)-3-phenyl-2,1-benzisoxazole, 9.8 g (0.15 mole) of potassium cyanide, 50 ml of water and 80 ml of dioxane was heated at reflux under nitrogen for 2.5 hr. The solution was cooled and diluted with 200 ml of methylene chloride. The layers were separated and the organic layer was washed twice with water (emulsion), dried over sodium sulfate and concentrated to give 8.6 g of a dark solid as residue. The solid was chromatographed on 180 g of silica gel eluting with 2% acetone in benzene and 5.8 g (80%) of solid was obtained from the eluant. An analytical sample, m.p. 107°-109° C. was prepared by recrystallizing with 2-propanol.

Provenance & Evidence