Synthesis
2-Nitro-4-bromobenzoic acid (10.0 g, 40.7 mmol) was dissolved in N,N-dimethylformamide (DMF, 100 mL). Cesium carbonate (Cs2CO3, 27.0 g, 81.3 mmol) and iodomethane (7.60 mL, 122.0 mmol) were added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, ethyl acetate (EtOAc, 250 mL) and water (100 mL) were added for extraction. The organic phase was separated and washed three times with water (100 mL) and then with saturated brine (50 mL), followed by drying with anhydrous sodium sulfate (Na2SO4). After filtration, the filtrate was concentrated using a rotary evaporator. The resulting product was dried under vacuum to give methyl 2-nitro-4-bromobenzoate (10.3 g, 97% yield).
References
[1] Patent: WO2006/19768, 2006, A1. Location in patent: Page column 87
[2] Patent: US2011/152246, 2011, A1. Location in patent: Page/Page column 186-187
[3] Patent: WO2017/120429, 2017, A1. Location in patent: Page/Page column 300
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6371 - 6390
[5] Patent: US2004/224983, 2004, A1. Location in patent: Page 15
