Chemical Properties
yellow crystalline powder
Uses
Methyl 2-bromo-5-nitrobenzoate may be used in chemical synthesis.
Synthesis
Methyl 2-bromo-5-nitrobenzoate was synthesized by esterification reaction using methanol and 2-bromo-5-nitrobenzoic acid as raw materials. The specific steps are as follows: in a dry reaction flask, 2-bromo-5-nitrobenzoic acid was dissolved in an appropriate amount of methanol, and a catalytic amount of concentrated sulfuric acid was added. The reaction mixture was stirred under reflux conditions for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, poured into ice water and neutralized with sodium bicarbonate solution to pH=7. Subsequently, the product was extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to afford methyl 2-bromo-5-nitrobenzoate in white crystalline form in 81% yield. The structure of the product was confirmed by 1H NMR and 13C NMR: 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 7.88 (d, J = 8.76 Hz, 1H), 8.18 (dd, J = 2.76 Hz, 1H), 8.66 (d, J = 2.74 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 53.12, 126.33, 126.61, 129.24, 133.12, 135.71, 146.70, 164.48.
References
[1] Journal of the American Chemical Society,
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 54 - 55
[3] Synthesis, 1999, # 7, p. 1246 - 1250
[4] Patent: US2009/131527, 2009, A1. Location in patent: Page/Page column 8
[5] Tetrahedron Letters, 2012, vol. 53, # 46, p. 6245 - 6249,5
