Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (07): 1004-1007. Previous Articles     Next Articles

Reports

叔丁基二甲硅氧基苯硼酸及羟基苯硼酸的制备

晁建平1,武文琼1,罗宣德2,凌仰之*,1   

  1. (1北京大学药学院药物化学系 北京 100083)
    (2中国药物研究开发中心 北京102206)
  • 收稿日期:2005-10-17 修回日期:2006-01-26 发布日期:2006-07-01
  • 通讯作者: 凌仰之

Preparation of t-Butyldimethylsiloxyphenyl Boronic Acids and Hydroxyphenylboronic Acids

CHAO Jian-Ping1,WU Wen-Qiong1,LUO Xuan-De2,LING Yang-Zhi*,1   

  1. (1 School of Pharmaceutical Science, Peking University, Beijing 100083)
    (2 National Institute of Pharmaceutical Research and Development, Beijing 100226)
  • Received:2005-10-17 Revised:2006-01-26 Published:2006-07-01
  • Contact: LING Yang-Zhi

p-, m- and o-bromophenols were first protected by t-butyldimethylchlorosilane, and then treated with Mg to form Grignard reagents. After reaction with tributylborate and selective hydrolysis, three t-butyldimethylsiloxy phenylboronic acids were ob-tained in yields 51% (p), 44% (m) and 40% (o), respectively. If dibutyl p- or m-siloxyphenylborate intermediates were hydrolyzed in strong acid, p or m-hydroxy- phenylboronic acids were achieved with yields of 14% and 65% respectively. But these hydroxyphenylbo-ronic acids were difficult to purify because the impurity hydroxyphenol was always formed spontaneously.

Key words: t-butyldimethylsiloxyphenylboronic acid, Grignard reagent, preparation, hydroxyphenylboronic acid