Synthesis
General procedure for the synthesis of 5-bromo-1,2,3-benzenetriol from 1-bromo-3,4,5-trimethoxybenzene: 7.44 g (30.24 mmol) of 3,4,5-trimethoxy-1-bromobenzene and 70 mL of anhydrous methylene chloride were added to a four-necked flask and the mixture was cooled to -78 °C. Subsequently, 325.0 g (99.8 mmol) of boron tribromide (BBr3) was slowly added dropwise, and after completion of the dropwise addition, the reaction mixture was continued to be stirred at -78 °C for 1 hour. Upon completion of the reaction, the mixture was slowly warmed to room temperature and carefully poured into 200 mL of ice water to precipitate the product. The precipitate was collected by filtration to give 6.8 g (quantitative yield) of 5-bromo-1,2,3-benzenetriol as a white powder. The m/z of 5-bromo-1,2,3-benzenetriol was analyzed by mass spectrometry to be 206.01 ([M + H]+).
References
[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 6, p. 1187 - 1196
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 18, p. 5031 - 5034
[3] Angew. Chem., 2017, vol. 129, # 18, p. 5113 - 5116,4
[4] Patent: JP6236813, 2017, B2. Location in patent: Paragraph 0184; 0185
[5] Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13437 - 13444
