Synthesis
General procedure for the synthesis of 2-(bromomethyl)benzeneboronic acid from 2-methylbenzeneboronic acid: 14.8 g (0.11 mol) of 2-methylbenzeneboronic acid was added to a 500 mL round bottom flask, followed by the addition of 380 mL of carbon tetrachloride, which was heated slightly until dissolved. A bromine solution was prepared by dissolving 17.9 g of bromine in 85 mL of carbon tetrachloride under light conditions. At the beginning of the reaction, a portion of the bromine solution was added quickly to keep the reaction solution light yellow. After the reaction was carried out for 2 hours, the reaction mixture was bleached with alkaline solution and subsequently filtered. The filter cake was washed five times with carbon tetrachloride and three times with hexane. Finally, the product was dried under vacuum to give 19.97 g of white powdery solid in 84.6% yield.
References
[1] Patent: CN103497211, 2016, B. Location in patent: Paragraph 0242; 0243
[2] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5875 - 5877
[3] Russian Chemical Bulletin, 2005, vol. 54, # 11, p. 2602 - 2611
[4] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
[5] Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2445 - 2450
