Sulfuric Acid → 3-Iodo-4-methyl-2-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

3-Amino-4-methyl-2-nitrobenzoic acid (13 g, 66 mmol) was taken up in 50 mL of DMSO and 30% aqueous sulfuric acid (150 mL) was added. The mixture was cooled to 0° C. and sodium nitrite (7 g, 99 mmol) dissolved in 20 mL of water was added slowly. The mixture was stirred for 1 h and potassium iodide (28 g, 166 mmol) dissolved in 50 mL of water was added. The mixture was allowed to stir at RT for 1 h. The mixture was extracted with ethyl acetate and the organic layer washed with an aqueous solution of 2 M sodium sulfite, water and brine. The organic layer was dried with sodium sulfate and concentrated under vacuum to give 3-iodo-4-methyl-2-nitrobenzoic acid (17 g, 84%) as a light brown solid. MS (M+H)+ 308.

Provenance & Evidence