204257-72-7

67-56-1

124700-40-9

204257-72-7

General procedure for the synthesis of methyl 2-fluoro-4-iodobenzoate from methanol and 2-fluoro-4-iodobenzoic acid: 1. 2-Fluoro-4-iodobenzoic acid (5.35 g, 20.1 mmol) was dissolved in methanol (30 mL, 741 mmol), and thionyl chloride (2.6 mL, 35.8 mmol) was added slowly and dropwise at 0 °C with stirring. 2. The reaction mixture was refluxed for 1 hour at 85 °C in an oil bath. 3. After completion of the reaction, excess methanol was removed by decompression distillation. 4. Benzene (20 mL) was added to the residue and again by decompression distillation. The reaction mixture was refluxed in an oil bath at 85 °C for 1 h. 3. After completion of the reaction, excess methanol was removed by distillation under reduced pressure. 4. Benzene (20 mL) was added to the residue, and the solvent was again removed by distillation under reduced pressure. 5. The residue was dissolved in ethyl acetate (150 mL), and the organic phase was washed with saturated sodium bicarbonate (200 mL) and brine (60 mL) in turn. 6. The organic layer was dried with anhydrous sodium sulfate, filtered, and decompressed. 7. Sodium sulfate was dried, filtered and concentrated under reduced pressure.7. The crude product was purified by silica gel column chromatography (150 mL SiO2, eluent ethyl acetate:hexane=1:48) to afford methyl 2-fluoro-4-iodobenzoate (5.3066 g, 94% yield) as a white crystalline solid with a melting point of 76-78 °C. The product was purified by 1H NMR (1H NMR) (1H NMR). The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (100.6 MHz, CDCl3), IR and LC-FAB-MS, and the data were in agreement with the literature reports.