Synthesis
Sodium methanolate (2.68 g, 49.59 mmol) was added to a solution of 5-bromo-3-fluoropyridine-2-carbonitrile (2.00 g, 9.93 mmol) in tetrahydrofuran (THF, 80 mL) at room temperature. The reaction mixture was stirred at 70 °C for 3 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 7 with a 3 M solution of HCl. The reaction mixture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 5-bromo-3-methoxypyridine-2-carbonitrile as a brown solid (2.00 g, 95% yield). Mass spectrum (MS): m/z = 213.0 [M + H]+.
References
[1] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 1219; 1220
[2] Patent: EP3275864, 2018, A1. Location in patent: Paragraph 0032; 0038; 0044; 0050; 0056; 0062
[3] Patent: WO2007/87488, 2007, A2. Location in patent: Page/Page column 24
