Synthesis
The general procedure for the synthesis of methyl 3-iodobenzoate from methanol and 3-iodobenzoic acid was as follows: 3-iodobenzoic acid (50 g, 0.20 mol) was dissolved in 300 mL of methanol, followed by the addition of 1 mL of concentrated sulfuric acid as a catalyst. The reaction mixture was heated to reflux at 80 °C for 24 hours. During the reaction, the water generated from the reaction was removed by distillation and methanol was replenished twice to maintain the reaction volume. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the solvent was removed by distillation under reduced pressure. 600 mL of ether was added to the residue and stirred overnight to induce the product to precipitate as a white precipitate. The product was separated by filtration and washed with cold water to afford methyl 3-iodobenzoate (51.3 g, 97% yield) as a white solid. NMR hydrogen spectrum (300MHz, CDCl3): δ8.34 (s, 1H), 7.97 (d, J=7.5Hz, 1H), 7.85 (d, J=7.2Hz, 1H), 7.15 (td, J1=7.8Hz, J2=2.7Hz, 1H), 3.89 (s, 3H). Gas chromatography-mass spectrometry (GC-MS) analysis: the calculated value of the molecular ion peak (m/z) C8H7IO2 was 262.0 and the measured value was 262.0.
References
[1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3197 - 3214
[2] Patent: WO2014/11477, 2014, A1. Location in patent: Page/Page column 29; 30
[3] Patent: WO2010/149620, 2010, A1. Location in patent: Page/Page column 45
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[5] Patent: JP5725475, 2015, B2. Location in patent: Paragraph 0028; 0029
