Synthesis
General procedure for the synthesis of 5-bromo-1,3-dihydroxymethylbenzene from dimethyl 5-bromoisophthalate: under argon protection, dimethyl 5-bromoisophthalate (4.54 g, 16.63 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0°C. Diisobutylaluminum hydride (80 mL, 80 mmol, 1 M solution in toluene) was slowly added to this solution via syringe. The reaction mixture was stirred at 0 °C for 1 h before the reaction was quenched with Rochelle's salt solution. The resulting two-phase mixture was continued to be stirred at room temperature for 12 hours. After completion of the reaction, post-treatment was carried out: the product was extracted with ether (2 x 50 mL), the organic layers were combined, washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated in vacuum to give (3-bromo-5-hydroxymethylphenyl)-methanol as a white solid (3.582 g, 99% yield).
References
[1] Patent: US6617346, 2003, B1
[2] Synthesis, 1998, # 12, p. 1742 - 1749
[3] Patent: EP2019104, 2009, A1. Location in patent: Page/Page column 26-27
[4] Patent: JP2005/120047, 2005, A. Location in patent: Page/Page column 141
[5] Chemische Berichte, 1989, vol. 122, p. 1365 - 1372
