Diiodomethane → 1-Fluoro-4-iodo-2-nitrobenzene

Participants

Reaction Steps

Add isoamyl nitrite (18.6 g, 160 mmol) to a suspension of 4-fluoro-3-nitrophenylamine (5.0 g, 32 mmol) in diiodomethane (150 mL). Stir under nitrogen at room temperature for 1 h. Heat at 70° C. for 1 h. Cool to room temperature and concentrate. Dilute with dichloromethane (500 mL) and water (100 mL). Collect the organic, concentrate and purify (silica gel chromatography, eluting with a gradient of 100:0 to 80:20 hexanes:ethyl acetate), to give the title compound as a yellow oil (1.22 g, 14%).

Provenance & Evidence