Ethyl 4-(bromomethyl)benzoate synthesis
- Product Name:Ethyl 4-(bromomethyl)benzoate
- CAS Number:26496-94-6
- Molecular formula:C10H11BrO2
- Molecular Weight:243.1
94-08-6
26496-94-6
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).
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Yield:26496-94-6 75%
Reaction Conditions:
with dmap;dicyclohexyl-carbodiimide in dichloromethane at 0; for 12 h;Inert atmosphere;
Steps:
Syntheses of compounds 6e-6j
General procedure: General Method H: To a solution of the acid (1.0 equiv.) in DCM, DCC (1.5 equiv.) was added and followed byalcohol (1.0 equiv.). Catalytic amount of DMAP was then added to the mixture. The reaction mixture was stirredovernight under N2. Water (5.0 mL) was added and the mixture was extracted with DCM. The organic phase waswashed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gelchromatography (EtOA/hexane) to afford pure products.
References:
Liu, Hao;Chen, Li;Zhou, Fei;Zhang, Yun-Xiao;Xu, Ji;Xu, Meng;Bai, Su-Ping [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 14,p. 3089 - 3096] Location in patent:supporting information
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52780-16-2
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