Uses
4-(Bromomethyl)benzoic Acid is an intermediate in the synthesis of Eprosartan (E590100), a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists used as an antihypertensive agent.
Synthesis
In a 100 mL round-bottomed flask, 40 mL of carbon tetrachloride was added as solvent, 3.00 g of p-methylbenzoic acid as starting material, 4.00 g of N-bromosuccinimide (NBS) as bromination reagent, and 0.1 g of azobisisobutyronitrile (AIBN) as initiator. The reaction mixture was stirred and refluxed at 90 °C and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature followed by filtration. The filter cake was washed with warm water to remove the succinimide by-products generated in the reaction. After drying, 4.02 g of p-bromomethylbenzoic acid was obtained with a melting point of 231-232°C in 84% yield.
References
[1] Chemistry - A European Journal, 2018, vol. 24, # 7, p. 1619 - 1630
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[3] Patent: CN108570012, 2018, A. Location in patent: Paragraph 0020; 0024; 0025
[4] Patent: CN108623537, 2018, A. Location in patent: Paragraph 0046; 0047; 0048
[5] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
