Selective α-Monobromination of Ketones with [Bmim]Br3

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Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (02): 236-238. Previous Articles Next Articles

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[Bmim]Br₃对酮的选择性单溴化反应

张胜建¹，乐长高*^,2

(¹浙江大学宁波理工学院宁波 315100)
(²东华理工学院应用化学系抚州 344000)

收稿日期:2005-04-11 修回日期:2005-08-17 发布日期:2006-01-21
通讯作者: 乐长高

Selective α-Monobromination of Ketones with [Bmim]Br₃

ZHANG Sheng-Jian¹,LE Zhang-Gao*^,2

(¹ Ningbo Institute of Technology, Zhejiang University, Ningbo 315100)
(² Department of Applied Chemistry, East China Institute of Technology, Fuzhou 344000)

Received:2005-04-11 Revised:2005-08-17 Published:2006-01-21

Contact: LE Zhang-Gao

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Abstract

Reaction of ketones with 1-butyl-3-methylimidazolium tribromide ([Bmim]Br₃) under solvent-free conditions at room temperature, selectively gave the corre-sponding α-bromoketones with 90%～96% yields. Compared to the known report, this method has the advantages of mild reaction condition, good yields, high selectivity and more environmental benignity.

Key words: ionic liquid, alkanone, 1-butyl-3-methylimidazolium tribromide, bromination

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ZHANG Sheng-Jian,LE Zhang-Gao*^,2. Selective α-Monobromination of Ketones with [Bmim]Br₃[J]. Chin. J. Org. Chem., 2006, 26(02): 236-238.

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[1]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[2]	Yong Xu, Yongxing Zhang, Jia Hu, Cheng Chen, Ye Yuan, Francis Verpoort. Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO₂ [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2542-2550.
[3]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[4]	Mengxia Zheng, Jing Zeng, Mailikezhati Meihemuti, Abudu Rexit Abulikemu. Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2121-2126.
[5]	Zihui Ning, Xinhua Peng, Rui Bai, Shanshan Liu, Zhuo Li, Linyu Jiao. Iridium Catalyzed C—H Amidation of Benzamides with Phosphoryl Azides in Ionic Liquids [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4484-4492.
[6]	Li Yang, Dong Shiyu, Qin Hongwei, Tang Bingyue, Gao Wentao, Chen Yu. A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2817-2826.
[7]	Li Shengnan, Zhao Wenxin, Liu Yujing, Liu Zhongqiu, Ying Anguo. Research Progress in the Application of Supported Functional Ionic Liquids in Organic Transformations [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1835-1846.
[8]	Wang Ligeng, Yu Qin, Feng Chun, Zhang Yan, Hu Jun. Efficient Synthesis of Dibromoalkanes and Iodoacetates from Olefins Using ZnAl-XO₃^--LDHs/LiX (X=Br, I) as Halogen Sources [J]. Chin. J. Org. Chem., 2019, 39(6): 1787-1793.
[9]	Li Jianxiao, Lin Shao, Huang Ruikang, Li Can, Yang Shaorong. Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid [J]. Chin. J. Org. Chem., 2019, 39(5): 1417-1423.
[10]	Wang Yinglei, Wan Zijuan, Luo Jun. Synthesis of Pyrazolo[1,2-b]phthalazine-5,10-diones Catalyzed by Poly(ethylene glycol) Grafted 4-Dimethylaminopyridine Functionalized Ionic Liquid [J]. Chin. J. Org. Chem., 2019, 39(2): 521-526.
[11]	Liu Xiaoqin, Wang Fei, Sun Hui, Zheng Mengya, Wang Hualan, Gong Kai. Synthesis of Tetrahydrobenzo[a]xanthen-11-ones Catalyzed byAcid Ionic Liquid Functionalized β-Cyclodextrin in Water [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2843-2850.
[12]	Ai Feng, Xie Zongbo, Jiang Guofang, Ji Jiujian, Le Zhanggao. Benzylic C(sp³)-H Functionalization Reaction of 2-Methylazaarenes in Ionic Liquid Aqueous Solution [J]. Chin. J. Org. Chem., 2018, 38(8): 2174-2181.
[13]	Zhang Tao, Wang Qiang. [Bmim]ZnBr₃-Promoted Tandem Reaction of Enaminoester and Allenic Ketones for the Synthesis of Substituted Nicotinate Derivatives [J]. Chin. J. Org. Chem., 2018, 38(2): 498-503.
[14]	Liu Baoyou, Zhang Peiwen. Progress of Ionic Liquids-Green Preparation and Application Research in Environmental Remediation [J]. Chin. J. Org. Chem., 2018, 38(12): 3176-3188.
[15]	Jiang Haifang, Zhang Min, Zhang Li, Chen Yali, Zhu Ning, Song Liping, Deng Hongmei. Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(9): 2399-2408.

[Bmim]Br3对酮的选择性单溴化反应