4-Fluorophenylhydrazine hydrochloride → 1-Azido-4-fluorobenzene

Participants

Reaction Steps

A solution of 262 mg of sodium nitrite dissolved in 2.0 ml of water was dropped into a solution of 3.09 g of 4-fluorophenylhydrazine hydrochloride in 20 ml of concentrated hydrochloric acid and 10 ml of diethyl ether under cooling with ice. Temperature of the reaction solution was raised to room temperature followed by stirring for 3 hours. The reaction solution was diluted with diethyl ether, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 1.01 g of the crude title compound as a brown oily substance.

Provenance & Evidence