[Synthesis]
General procedure for the synthesis of ethyl 2-fluoro-5-iodobenzoate from ethanol and 2-fluoro-5-iodobenzoic acid:
2-Fluoro-5-iodobenzoic acid (Oakwood, 0.99 g, 3.72 mmol) and H2SO4 (198 μL, 3.72 mmol) were added to EtOH (7.4 mL). The reaction mixture was stirred at 100 °C overnight. After completion of the reaction, the mixture was concentrated in vacuum. The crude product was purified by fast column chromatography (gradient of 0 to 10% EtOAc/hexane) to afford the title compound ethyl 2-fluoro-5-iodobenzoate (916 mg, 84%) as a colorless oil.
1H NMR (CDCl3) δ 8.24 (dd, J = 6.8, 2.4 Hz, 1H), 7.81 (ddd, J = 8.8, 4.5, 2.4 Hz, 1H), 6.93 (dd, J = 10.3, 8.6 Hz, 1H), 4.41 (q, J = 7.0 Hz, 2H), 1.42 (t, J = 7.2 Hz, 3H). |