Sulfuric Acid → 6-Chloro-3'-fluoro-4-iodobiphenyl-3-ol

Participants

Reaction Steps

N-Iodosuccinimide (261 mg, 1.16 mmol) was added to a mixture of 6-chloro-3′-fluorobiphenyl-3-ol (Preparation 100, 270 mg, 1.21 mmol) and concentrated sulphuric acid (24 μL, 0.43 mmol) in acetic acid (3 mL) and dichloromethane (3 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with dichloromethane (10 mL) and washed with sodium metabisulfite (0.5M, 10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with heptane:dichloromethane (70:30) to give the title compound (193 mg, 46%) as a pale yellow solid.

Provenance & Evidence