METHYL 4-BROMO-2-BROMOMETHYL-BENZOATE

Uses

Methyl 4-bromo-2-(bromomethyl)benzoate is used as pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of methyl 4-bromo-2-bromomethylbenzoate from methyl 4-bromo-2-methylbenzoate: a mixture of methyl 4-bromo-2-methylbenzoate (1 g, 4.4 mmol), N-bromosuccinimide (NBS, 0.80 g, 4.4 mmol), benzoyl peroxide (BPO, 56 mg, 0.23 mmol) and carbon tetrachloride (CCl4 , 20 mL) mixture was stirred and reacted at 85°C for 2 hours. Upon completion of the reaction, the mixture was filtered through a silica gel pad and the filtrate was subsequently concentrated to afford the target product methyl 4-bromo-2-bromomethylbenzoate (1.3 g, 97% yield).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 6, p. 1324 - 1328
[2] Patent: WO2018/68017, 2018, A1. Location in patent: Page/Page column 126
[3] Patent: WO2007/339, 2007, A1. Location in patent: Page/Page column 35-36
[4] Patent: US2010/222363, 2010, A1. Location in patent: Page/Page column 13
[5] Patent: WO2007/337, 2007, A1. Location in patent: Page/Page column 30