Sulfuric Acid → 2-Iodo-4-(trifluoromethoxy)phenol

Participants

Reaction Steps

To a suspension of N-iodosuccinimide (6.95 g, 31 mmol) in glacial acetic acid (2 ml) was added 4-trifluoromethoxy phenol (4.0 ml, 31 mmol) and, after 5 minutes, concentrated sulphuric acid (0.5 ml, 9 mmol). The pale brown suspension was stirred at ambient temperature under nitrogen for 48 hours before diluting with water and extracting with dichloromethane. The organic extract was washed with water, saturated aqueous sodium thiosulfate solution and water, dried over anhydrous magnesium sulfate and decolorizing charcoal added. The resulting suspension was left to stand for 30 minutes before filtering through a short pad of silica gel eluting with dichloromethane. The solvent was concentrated in vacuo to afford the title compound as an oil (1.18 g, 12%).

Provenance & Evidence