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高等学校化学研究 ›› 2004, Vol. 20 ›› Issue (6): 734-737.

• Articles • 上一篇    下一篇

A Convenient and Practical Prepapation of Acetylphenyl Boronic Acids

CHAO Jian-ping1, WANG Wei1, WU Wen-qun1, LUO Xuan-de2, LING Yang-zhi1   

  1. 1. School of Pharmaceutical Science, Peking University, Beijing 100083, P. R. China;
    2. National Institutes of Pharmaceutical Research and Development, Beijing 100226, P. R. China
  • 收稿日期:2003-12-09 出版日期:2004-12-24 发布日期:2011-08-06
  • 基金资助:

    Supported by the National Nature Science Foundation of China(No.3017110).

A Convenient and Practical Prepapation of Acetylphenyl Boronic Acids

CHAO Jian-ping1, WANG Wei1, WU Wen-qun1, LUO Xuan-de2, LING Yang-zhi1   

  1. 1. School of Pharmaceutical Science, Peking University, Beijing 100083, P. R. China;
    2. National Institutes of Pharmaceutical Research and Development, Beijing 100226, P. R. China
  • Received:2003-12-09 Online:2004-12-24 Published:2011-08-06
  • Supported by:

    Supported by the National Nature Science Foundation of China(No.3017110).

PDF (PC)

摘要： A practical and scalable synthesis route of acetylphenylboronic acids is described. Bromoacetophenones(compounds 3a, 3b) were ketalized with ethylene glycol and triethyl orthoformate to give bromo ketals(compounds 4a_4c) in 60_80% yields. Compounds 4a_4b were treated with a Grignard reagent and then exchanged with borate to give p- and m- acetylphenyl boronic acids(compounds 5a and 5b) in 80% and 56% yields, respectively. The o-form(compound 5c) was obtained in 61% yield via the BuLi method.

关键词: p-, m-, o-Acetylphenylboronic acid, Grignard reaction, Mg- and Li-halogen exchange

Abstract: A practical and scalable synthesis route of acetylphenylboronic acids is described. Bromoacetophenones(compounds 3a, 3b) were ketalized with ethylene glycol and triethyl orthoformate to give bromo ketals(compounds 4a_4c) in 60_80% yields. Compounds 4a_4b were treated with a Grignard reagent and then exchanged with borate to give p- and m- acetylphenyl boronic acids(compounds 5a and 5b) in 80% and 56% yields, respectively. The o-form(compound 5c) was obtained in 61% yield via the BuLi method.

Key words: p-, m-, o-Acetylphenylboronic acid, Grignard reaction, Mg- and Li-halogen exchange