Sodium Azide → 2-Chloro-3-fluoroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-3-fluorobenzoic acid (4 g, 23 mmol) in CHCl3 (50 mL), sulfonic acid (64 mL) was added and then sodium azide (2.62 g, 1.75 mmol) was added by portion. After addition, the reaction mixture was stirred at 50° C. for 16 hours. The solvent was evaporated and basicified with ammonium hydroxide at ice-bath. Then was extracted with ethyl acetate (3×). The combine organic phase was dried and conc. to give the desired product (2.61 g, 78%). LC-MS m/z 146.2 (M+).

Provenance & Evidence