Synthesis
General procedure for the synthesis of ethyl 2-iodobenzoate from ethanol and 2-iodobenzoic acid: 2-iodobenzoic acid (10 g) was dissolved in 60 mL of ethanol and 5 mL of concentrated H2SO4 was added as a catalyst. The reaction mixture was placed in an oil bath at 78 °C with electromagnetic stirring for 5 hours. Upon completion of the reaction, excess ethanol was removed under reduced pressure using a rotary evaporator. Water and ethyl acetate were added to the residue to separate the organic layer. The organic layer was washed three times sequentially with water and saturated sodium bicarbonate solution. Finally, the organic layer was dried with anhydrous Na2SO4, filtered and the solvent was removed by distillation to afford ethyl 2-iodobenzoate in 99% yield.
References
[1] Synthetic Communications, 2017, vol. 47, # 12, p. 1175 - 1184
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4822 - 4825
[3] Tetrahedron Letters, 2014, vol. 55, # 3, p. 690 - 693
[4] Patent: US2010/216853, 2010, A1. Location in patent: Page/Page column 19-20
[5] Tetrahedron Letters, 1996, vol. 37, # 35, p. 6375 - 6378
