Application
Methyl 5-bromo-2-iodobenzoate belongs to the benzoic acid derivatives and is mainly used as an intermediate in organic synthesis and pharmaceutical chemistry. It can be used to prepare preservatives, dyes, and drug molecules.
Chemical Properties
off-white powder
Synthesis
Concentrated sulfuric acid (10 mL) was added dropwise to a stirred solution of methyl 2-iodobenzoate (5.0 g, 19.08 mmol, 1.0 eq.) and N-bromosuccinimide (NBS, 3.73 g, 20.99 mmol, 1.1 eq.) in acetic acid (10 mL), keeping the reaction temperature between 20-40 °C. The reaction mixture was stirred at room temperature for 88 hours and then warmed up to 50°C and continued stirring for 4 hours. Upon completion of the reaction, the mixture was cooled to 10 °C and the reaction was quenched with cold water (40 mL) and subsequently extracted with dichloromethane (DCM, 3 x 50 mL). The organic layers were combined and washed sequentially with 5% sodium bicarbonate solution (2 × 50 mL), 10% sodium sulfite solution (50 mL), and water (50 mL), then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product methyl 5-bromo-2-iodobenzoate. The crude product was purified by rapid column chromatography on silica gel, the eluent being a hexane solution of 10% ethyl acetate. The pure grade was collected and the solvent was evaporated under reduced pressure to give methyl 5-bromo-2-iodobenzoate as an off-white solid (5 g, 77% yield). NMR hydrogen spectrum (400 MHz, CDCl3) δppm: 3.94 (s, 3H), 7.26-7.29 (m, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.93 (d, J=8.8 Hz, 1H).
References
[1] Patent: WO2018/15879, 2018, A1. Location in patent: Page/Page column 81
[2] Patent: US2004/92521, 2004, A1. Location in patent: Page/Page column 16-20; 46
[3] Patent: US2005/256118, 2005, A1. Location in patent: Page/Page column 18-19
[4] Patent: US2005/256309, 2005, A1. Location in patent: Page/Page column 20-21; 36
[5] Patent: US2005/272728, 2005, A1. Location in patent: Page/Page column 19-20
