Iodine → 5-(Dimethylamino)-2-iodophenol

Participants

Reaction Steps

Iodine (6.35 g, 25 mmol) in methylene chloride (300 mL) was added dropwise over 3 h to a stirred suspension of thallium(I) acetate (7.90 g, 30 mmol) and 3-dimethylaminophenol (3.43 g, 25 mmol) in methylene chloride (300 mL). The resulting mixture was stirred at room temperature for 24 h and filtered. Evaporation of the solvents and chromatography of the residue over silica gel using 0-5% diethyl ether in hexanes gave 5-dimethylamino-2-iodophenol (2.35 g, 36%).

Provenance & Evidence