Sulfuric Acid → 2-Iodo-4-methoxybenzoic acid

Participants

Reaction Steps

To a mixture of 50% sulfuric acid (150 ml) and 4-methoxyanthranilic acid (12 g) at 5°-10° C. was added sodium nitrite (5.5 g) in water, followed 10 minutes later by NaI (16.5 g) in water (30-50 ml). The reaction mixture was warmed to room temperature and stirred for 2 hours, then was heated at 60°-70° C. for 10 minutes, followed by stirring at room temperature for 1 hour. The reaction mixture was extracted with ether (4×125 ml) and the combined ether extracts were washed with water (50 ml×2), dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica gel eluting with ether to afford 12 g of 2-iodo-4-methoxybenzoic acid.

Provenance & Evidence