Iodine → 5-Chloro-4-iodo-2-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-amino-5-chloro-2-methoxybenzoic acid (5 g, 24.8 mmol) in water (10 mL) at 0° C., concentrated sulfuric acid (50 mL) was added. Then a solution of NaNO2 (1.9 g, 27.3 mmol) in water (10 mL) was added dropwise while keeping the internal temperature around 0° C. KI (4.5 g, 27.3 mmol) and I2 (3.5 g, 13.64 mmol) were dissolved in water and added dropwise to the stirred reaction mixture. The reaction was stirred at 5° C. for 2 h and then extracted with ethyl acetate. The organic layer was washed with water, Na2SO3 (aq, 10%) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford desired product (1.55 g, 19% yield). ESI-MS m/z: 311.1[M+H]+.

Provenance & Evidence