2-Fluoroaniline → 4-Bromo-2-fluoroaniline

Participants

Reaction Steps

To a solution of o-fluoroaniline (3.9 g) in methylene chloride (50 ml), cooled to -20° under nitrogen, is added a solution of 2,4,4,6-tetrabromocyclohexadienone (35 mmol) in methylene chloride. After several hours, reaction is poured into 15% NaOH solution. The layers are separated and the organic fraction shaken against 15% NaOH solution. The methylene chloride fraction is washed with saturated NaCl solution, dried over calcium sulfate and evaporated to yield 4-bromo-2-fluoroaniline.

Provenance & Evidence