Synthesis
1,9-Nonanediol (20 g, 0.125 mol) was dissolved in toluene (500 mL) in a 500 mL round bottom flask fitted with a Dean-Stark water separator. Hydrobromic acid (48%, 21 mL, 188 mmol) was slowly added to this solution, followed by heating and refluxing the reaction mixture for 30 h, during which time the resulting water was removed by means of a Dean-Stark water separator. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete consumption of 1,9-nonanediol. Upon completion of the reaction, the mixture was cooled to room temperature and washed sequentially with 1 M hydrochloric acid (100 mL), 1 M sodium hydroxide solution (100 mL), water (100 mL) and saturated saline (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by fractional distillation to give 9-bromo-1-nonanol in 94% yield. Boiling point: 124-128°C/2 mmHg (literature value: 125-126°C/2 mmHg).
References
[1] Patent: WO2017/171674, 2017, A1. Location in patent: Page/Page column 3; 4
[2] Tetrahedron, 1997, vol. 53, # 21, p. 7255 - 7266
[3] Chemical Research in Toxicology, 2012, vol. 25, # 10, p. 2253 - 2260
[4] Journal of Fluorine Chemistry, 2003, vol. 123, # 2, p. 255 - 259
[5] Molecules, 2013, vol. 18, # 5, p. 5201 - 5208
