叔丁基二甲硅氧基苯硼酸及羟基苯硼酸的制备  

Preparation of t-Butyldimethylsiloxyphenyl Boronic Acids and Hydroxyphenylboronic Acids

作　　者：晁建平[1] 武文琼[1] 罗宣德 凌仰之[1] 

机构地区：[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

出　　处：《有机化学》2006年第7期1004-1007,共4页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.3017110)资助项目.

摘　　要：以邻、间、对三种溴酚为原料,经叔丁基二甲基氯硅烷保护酚基后制成格氏试剂,然后与硼酸酯反应,选择性水解得到了邻、间、对-叔丁基二甲硅氧基苯硼酸,收率分别为51%,44%和40%.将对位、间位的硼酸酯中间体3a,3b用强酸水解可得到间羟基苯硼酸(产率65%)和对羟基苯硼酸(产率14%),但发现它们极难纯化,这是由于羟基硼酸极易生成苯二酚之故.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 obtained 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-hydroxyphenylboronic acids were achieved with yields of 14% and 65% respectively. But these hydroxyphenylboronic acids were difficult to purify because the impurity hydroxyphenol was always formed spontaneously.

关 键 词：羟基苯硼酸 叔丁基二甲硅氧基苯硼酸 格氏试剂 制备 

分 类 号：O627.81[理学—有机化学]