Synthesis
General procedure for the synthesis of methyl 3-bromomethylbenzoate from methyl m-methylbenzoate: 30 mL of carbon tetrachloride (CCl4) and 7.9 g of methyl m-methylbenzoate were added to a dry 100 mL three-necked flask, and after dissolution, 0.23 g of AIBN (azobisisobutyronitrile) and 9.36 g of NBS (N-bromosuccinimide) were sequentially added in three additions (with an interval of about 2-3 hours). The reaction system was heated to 70°C and the color of the reaction solution was observed to change gradually from yellow to orange and finally to white. The reaction was monitored by TLC (eluent: cyclohexane/ethyl acetate = 5:1) until the reaction was almost complete. At the end of the reaction, the resulting succinimide and unreacted N-bromosuccinimide were removed by filtration. The filtrate was rotary evaporated to give 11.5 g of a yellow oily product, methyl 3-bromomethylbenzoate, in 95% yield.
References
[1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 14, p. 2506 - 2511
[2] Patent: CN106146413, 2016, A. Location in patent: Paragraph 0027; 0028
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 7 - 17
[4] Molecules, 2016, vol. 21, # 12,
[5] Patent: WO2018/169777, 2018, A1. Location in patent: Paragraph 0227
