Chlorine → 4-fluoro-N-hydroxybenzenecarboximidoyl chloride

Participants

Reaction Steps

A solution of 25 g of 4-fluorobenzaldoxime in 200 ml of chloroform was cooled to 0° to -10°. From a pressure bottle, 14.2 g of chlorine was run into a flask cooled by dry ice-acetone and allowed to distill into the aldoxime solution, the solution being maintained at 0° ± 5°. The reaction mixture was stirred for one hour in an ice bath while nitrogen was bubbled through the solution. The chloroform was evaporated to leave an oil to which hexane was added quickly. The solid which separated was recrystallized from hexane to give 15.0 g of 4-fluorobenzohydroximoyl chloride, m.p. 74.5°-75°. The ir spectrum was consistent with the assigned structure.

Provenance & Evidence