874792-20-8

At room temperature, 6-bromo-4-chloroquinoline (12.12 g, 50 mmol) was dissolved in methanol (200 mL) followed by addition of sodium methanolate (13.50 g, 250 mmol). The reaction mixture was transferred to a sealed reaction flask, heated to 120 °C and maintained for 15 hours. After completion of the reaction, it was cooled to room temperature and methanol was removed by distillation under reduced pressure. The residue was diluted with water and the resulting solid was collected by filtration and washed with deionized water. The solid was dried over air to give 10.8 g of 6-bromo-4-methoxyquinoline in 90.8% yield as a white solid. The product could be further purified by acetonitrile recrystallization.EI-HRMS analysis result: m/e calculated value C10H8BrNO (M+) 236.9789, measured value 236.9784.

[1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 8, p. 730 - 734
[2] Patent: US2006/63805, 2006, A1. Location in patent: Page/Page column 9
[3] Patent: WO2010/20363, 2010, A1. Location in patent: Page/Page column 115