Methyl 2-bromomethylbenzoate

Uses

Methyl 2-Bromomethylbenzoate is a reactant in the preparation of Methyl 2-((4-(2-(2-methylphenoxy)acetyl)piperazin-1-yl)methyl)benzoate with neuroprotective activity.

Synthesis

General procedure for the synthesis of methyl 2-bromomethylbenzoate from methyl o-toluate: (2) 1.50 g (10 mmol) of methyl o-toluate was added to a 250 mL round-bottom flask and dissolved in 80 mL of carbon tetrachloride. Subsequently 1.98 g (11 mmol) of N-bromosuccinimide (NBS) and 48 mg (0.2 mmol) of benzoyl peroxide (BPO) were added. The mixture was heated to reflux for 1.5 h to ensure complete reaction. Upon completion of the reaction, insoluble material was removed by filtration and the solvent was subsequently evaporated to give methyl 2-bromomethylbenzoate. The reaction was quantitative.

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 24, p. 4667 - 4677
[2] Chemical Communications, 2010, vol. 46, # 13, p. 2227 - 2229
[3] Patent: US2011/237786, 2011, A1. Location in patent: Page/Page column 7
[4] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 9, p. 1132 - 1148
[5] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 9, p. 1359 - 1360