Synthesis
General procedure for the synthesis of 2-fluoro-3-iodobenzoic acid from 2-fluoro-3-iodobenzonitrile: A mixture of 2-fluoro-3-iodobenzonitrile (5.00 g, 20.2 mmol), dioxane (16 mL), and concentrated sulfuric acid (25 mL) was heated to 115 °C and reacted for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble material. Water was added to the filtrate and the aqueous phase was extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-fluoro-3-iodobenzoic acid (4.42 g, 82% yield) as a white solid. Mass spectrum (LRMS) m/z: 265 ([M-H]-). 1H-NMR (CDCl3) δ: 6.94-7.01 (m, 1H), 7.90-7.97 (m, 2H).
References
[1] Patent: EP2113503, 2009, A1. Location in patent: Page/Page column 32
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6253 - 6257
