2-Iodophenylacetic acid is a synthetic intermediate that is widely used in the chemical, pharmaceutical and cosmetic industries. 2-Iodophenylacetic acid is also used as a reagent to synthesize Cepharanone B, a natural and potentially antineoplastic aristolactam that is found in Piper longum (a medicinal plant native to India).
2-Iodophenylacetic acid may be used in the preparation of:
2-iodophenylacetyl chloride
3,4-dimethoxyphenyl 2-iodophenylacetate
N-{2-[2-(2-iodophenyl)-acetylamino]-ethyl}-2-(3,4- dichlorophenyl)-acetamide
synthesis of 2-Iodophenylacetic acid: The anthranilic acid solution was acidified with sulfuric acid to pH = 1 followed by a diazotization reaction. The diazonium was added dropwise to the potassium iodide-sulfuric acid solution (3.5 g KI, 1.0 mL concentrated H2SO4, 5 mL water) preheated to 60-70 °C, stirred for 30 min, placed overnight, and filtered to obtain the product. Recrystallization with 50% ethanol aqueous solution gave 3.83 g of 2-iodophenylacetic acid, the yield was 73% (calculated as o-nitrophenylacetic acid), and the melting point was 113-115 °C (117 °C reported in the literature).
2-Iodophenylacetic acid is a substituted acetic acid that can be prepared from 2-iodobenzyl cyanide. It undergoes palladium-catalyzed reaction with allenes to form 1,3-butadienes. 2-Iodophenylacetic acid also undergoes photolysis in carbon tetrachloride to form the corresponding chloro compound.
