Hydrochloric Acid → 2-Bromo-1-fluoro-4-iodobenzene

Participants

Reaction Conditions

Reaction Steps

Add at 0° C. a solution of sodium nitrite (2.0 g, 28.9 mmol) in water (15 mL) to a suspension of 3-bromo-4-fluorophenylamine (5.0 g, 26.3 mmol) in a 6 N aqueous solution of hydrochloric acid (25 mL) at 0° C. slowly over 10 min. Stir the mixture at 0° C. for 5 min. Add this solution to a solution of potassium iodide (4.37 g, 26.3 mmol) in water (125 mL) via syringe at 0° C. under nitrogen over 15 min. Stir at 0° C. for 30 min. Warm to room temperature. Extract with four times with dichloromethane (100 mL), dry (sodium sulfate), filter, and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 95:5 hexanes:ethyl acetate to give the title compound as a colorless oil (5.83 g, 74%).

Provenance & Evidence