Sulfuric Acid → HCID 66652905, compound

Participants

Reaction Steps

Concentrated sulfuric acid (0.78 mL. 15.0 mmol) was added to a mixture of 4-fluoro-3-(trifluoromethyl)phenol (8.00 g, 44.4 mmol) and N-iodosuccinimide (5.00 g, 22.2 mmol) in acetic acid (40 mL) at 0° C. After 1 hour, the ice bath was removed and an additional portion of N-iodosuccinimide (1.50 g. 6.67 mmol) added. After an additional 1 hour at ambient temperature, the final portion of N-iodosuccinimide (1.0 g, 4.4 mmol) was added. The reaction mixture was stirred for 1 hour then diluted with water (300 mL), treated with 20 wt % aqueous sodium thiosulfate, and extracted with ether (3×100 mL). The combined organic layers were washed with aqueous sodium thiosulfate then brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by automated silica gel flash chromatography (100% hexanes to 50% dichloromethane in hexanes gradient elution) to afford the title compound as a yellow oil (8.1 g).

Provenance & Evidence