One-step for the preparation of α-haloacetal of ketones with N-bromosuccinimide/N-chlorosuccinimide (NBS/NCS) and ethylene glycol

被引：8
作者：
Zheng, Zubiao [1 ]
Han, Bingbing [1 ]
Wu, Fang [1 ]
Shi, Tengfei [1 ]
Liu, Jie [1 ]
Zhang, Yong [1 ]
Hao, Jialong [1 ]
机构：
[1] Huangshan Univ, Dept Chem, Huangshan 245041, Anhui, Peoples R China
来源：
TETRAHEDRON | 2016年 / 72卷 / 48期
关键词：
Ketones; alpha-Haloacetalization; N-Halosuccinimide; alpha-Haloacetals of ketones; One-step; AROMATIC-COMPOUNDS; EFFICIENT METHOD; BROMINATION; MILD; HALOGENATION;
D O I：
10.1016/j.tet.2016.05.064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new process that could directly prepare alpha-haloacetal of ketones from various ketones with N-halosuccinimide (NBS/NCS) and ethylene glycol in one step without any other catalysts was reported. The effects of solvents, NBS/NCS and reaction temperature were investigated. Under the optimal condition, most of alpha-haloacetals of ketones were obtained in 90-100% yield. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7738 / 7743
页数：6
相关论文
共 33 条
  • [1] Akihiro I., [No title captured], Patent No. [W02004014887, 2004014887]
  • [2] ACTION OF FUNGICIDAL TRIAZOLES OF THE DICLOBUTRAZOL SERIES ON USTILAGO-MAYDIS
    BALDWIN, BC
    WIGGINS, TE
    [J]. PESTICIDE SCIENCE, 1984, 15 (02): : 156 - 166
  • [3] Bharadwaja S. T. P., 2015, ORG LETT, V17, P71
  • [4] Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH
    Chen, Zizhan
    Zhou, Bin
    Cai, Huihua
    Zhu, Wei
    Zou, Xinzhuo
    [J]. GREEN CHEMISTRY, 2009, 11 (02) : 275 - 278
  • [5] PHOSPHONIUM TRIBROMIDES - BROMATION AGENTS FROM ORGANIC SUBSTRATES
    CRISTAU, HJ
    TORREILLES, E
    MORAND, P
    CHRISTOL, H
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 25 (03): : 357 - 367
  • [6] Metal Organic Frameworks as Solid Acid Catalysts for Acetalization of Aldehydes with Methanol
    Dhakshinamoorthy, Amarajothi
    Alvaro, Mercedes
    Garcia, Hermenegildo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 3022 - 3030
  • [7] TRICYCLO [5.3.0.02,6]DECANE SYSTEM - PHOTODIMERS OF CYCLOPENTENONE
    EATON, PE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (12) : 2344 - &
  • [8] Fournier M. J. L, 2001, E EROS
  • [9] Advancing the Mechanistic Understanding of an Enantioselective Palladium-Catalyzed Alkene Difunctionalization Reaction
    Jensen, Katrina H.
    Webb, Jonathan D.
    Sigman, Matthew S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) : 17471 - 17482
  • [10] DELTA2,6-HEXALIN-1,5-DIONE
    JOHNSON, WS
    WILLIAMSON, KL
    DOLFBASS, J
    [J]. TETRAHEDRON, 1963, 19 (06) : 861 - &
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