Iodine → 5-Ethyl-2-iodophenol

Participants

Reaction Steps

Iodine (6.35 g, 25 mmol) in methylene chloride (360 mL) was added dropwise over 3 h to a stirred suspension of 3-ethyl-phenol (3.05 g, 25 mmol) and thallium (I) acetate (7.90 g, 30 mmol) in methylene chloride (300 mL). The resulting mixture was stirred at room temperature for 24 h and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% ethyl acetate in hexanes to afford 5-ethyl-2-iodophenol (3.49g, 56%).

Provenance & Evidence