Uses
2-Bromopyridine-4-carboxylic acid methyl ester is a kind of important medicine intermediate, used as initiator during the synthesis of polymer brushes with single-walled carbon nanotubes as backbones.
Synthesis
To a 250 mL round bottom flask was added a methanol (100 mL) solution of 2-bromo-4-pyridinecarboxylic acid (10 g, 49.50 mmol, 1.00 equiv) and concentrated sulfuric acid (98%, 5 mL). The reaction mixture was stirred at 70 °C overnight. Upon completion of the reaction, the solution was concentrated under reduced pressure to remove the solvent. The residue was dissolved in 200 mL of ethyl acetate (EtOAc) and washed with saturated sodium bicarbonate solution (3 x 150 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give 10 g (94% yield) of methyl 2-bromopyridine-4-carboxylate as a colorless oil.
References
[1] Patent: WO2016/138335, 2016, A1. Location in patent: Paragraph 00319
[2] Patent: WO2016/34675, 2016, A1. Location in patent: Page/Page column 69
[3] Patent: US2011/111046, 2011, A1. Location in patent: Page/Page column 18
[4] Patent: WO2011/58473, 2011, A1. Location in patent: Page/Page column 37
[5] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7441 - 7448
