Sulfuric Acid → 5-Chloro-3-iodo-2-methyl-benzoic acid

Participants

Reaction Steps

To a solution of 5-chloro-2-methylbenzoic acid (10.0 g, 58.6 mmol) in sulfuric acid (75 mL, 1407 mmol) was added portionwise 1,3-diiodo-5,5-dimethylimidazolidine -2,4-dione (12.0 g, 31.6 mmol). The reaction turned very dark and quickly formed a thick suspension. The reaction was stirred for 2 h, at which time it was poured into ice water (˜500 mL) and stirred for 30 min to break up the solids. The precipitate was filtered off, washed with water, and dried under vacuum to give 5-chloro-3-iodo-2-methylbenzoic acid (17.3 g, 50.2 mmol, 86% yield) as a light beige solid. 1H NMR (400 MHz, DMSO-d6) δ 13.48 (br. s., 1H), 8.11 (d, J=2.27 Hz, 1H), 7.73 (d, J=2.27 Hz, 1H), 2.54 (s, 3H).

Provenance & Evidence