Potassium Iodide → 2-Iodo-3-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To 2-amino-3-methoxybenzoic acid (1.00 g, 5.98 mmol) in 25% aqueous hydrochloric acid (8 ml) at 0° C. was added sodium nitrite (0.45 g, 6.50 mmol) in water (3 ml). This solution was added drop-wise to a solution of potassium iodide (15.8 g, 59.3 mmol) in water (60 ml) and allowed to warm to 25° C. then stirred for 16 h. The reaction mixture was quenched with 1 N aqueous sodium bicarbonate until the pH became basic. The solution was extracted with methylene chloride and the organic dried over sodium sulfate, filtered, and concentrated to give a purple oil. The residue was purified by column chromatography, eluting with 10% methanol in dichloromethane. Pure fractions were concentrated to afford (0.623 g, 38%) of 2-iodo-3-methoxybenzoic acid. MS (EI) for C8H7IO3: 279 (MH+).

Provenance & Evidence