Application
6-Bromo-4-hydroxyquinoline is an important intermediate in the metallurgical, dye, polymer, and agrochemical industries. It can also be used as a disinfectant, preservative, and solvent.
Synthesis
4.1.7 Synthesis of 6-bromoquinolin-4-ol (10): 6-bromo-4-hydroxyquinoline-3-carboxylic acid (9) (5.0 g, 18.73 mmol) was placed in a 100 mL round-bottomed flask and diphenyl ether (Ph2O, 30 mL) was added. The reaction mixture was stirred at 260 °C for 2 hours. After completion of the reaction, it was cooled to 60 °C and petroleum ether (30 mL) was added to precipitate the product. The suspended solid was collected by filtration and washed sequentially with petroleum ether and ethyl acetate (EtOAc). Finally, the product was dried under reduced pressure to afford the title compound 6-bromoquinolin-4-ol (10) (3.21 g, 14.39 mmol, 77% yield) as a brown solid.ESI-MS: m/z = 224 [M + H]+.
References
[1] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[2] Patent: US2006/63805, 2006, A1. Location in patent: Page/Page column 9
[3] Patent: WO2012/116237, 2012, A2. Location in patent: Page/Page column 120
[4] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0557; 0558
[5] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
