Iodine → 5-Fluoro-2-iodo-4-(trifluoromethyl)phenol

Participants

Reaction Steps

A solution of iodine (0.874 g, 3.44 mmol) in chloroform (17.1 mL) was added in a drop-wise manner over 1.5 hours to a mixture of 3-fluoro-4-(trifluoromethyl)phenol (Preparation 7, 620 mg, 3.4 mmol) and silver trifluoroacetate (0.760 g, 3.44 mmol) in chloroform (3.4 mL). On completion of the addition, the reaction mixture was stirred for 1 hour. The reaction mixture was then filtered through diatomaceous earth, and the filtrate washed successively with 10% w/v aqueous sodium thiosulfate, half-saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated onto diatomaceous earth. The residue was purified by automated silica gel flash chromatography (100% hexanes to 50% dichloromethane in hexanes gradient elution) and concentrated in vacuo to afford the title compound as a light yellow oil (579 mg).

Provenance & Evidence