Ethyl 4-(bromomethyl)benzoate

Uses

4-​(bromomethyl)​-​Benzoic acid ethyl ester is a brominated aromatic building block used in various syntheses such as the preparation of imidazoles and imidazo-fused heterocycles.

Uses

4-(bromomethyl)-Benzoic acid ethyl ester is a brominated aromatic building block used in various syntheses such as the preparation of imidazoles and imidazo-fused heterocycles.

Synthesis

General procedure for the synthesis of ethyl 4-(bromomethyl)benzoate from ethyl p-methylbenzoate: to a stirred solution of ethyl 4-methylbenzoate (5 g, 30.49 mmol) in carbon tetrachloride (35 ml) was added sequentially N-bromosuccinimide (5.90 g, 33.53 mmol) and benzoyl peroxide (720 mg, 1.52 mmol). The reaction mixture was heated under reflux conditions for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and subsequently filtered. The filtrate was concentrated by vacuum evaporation to give the colorless oily product ethyl 4-(bromomethyl)benzoate (7.25 g, 98% yield).

References

[1] Chinese Journal of Chemistry, 2012, vol. 30, # 8, p. 1906 - 1908
[2] Patent: WO2009/109999, 2009, A1. Location in patent: Page/Page column 68
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[4] Synthesis (Germany), 2018, vol. 50, # 24, p. 4933 - 4939
[5] Tetrahedron, 2007, vol. 63, # 36, p. 8891 - 8901