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Study on Synthesis of Halopyridinylboronic Acid

Author: SongAiPing
Tutor: ZhuWeiHong；FanAiLong
School: East China University of Science and Technology
Course: Industry Technology and Engineering
Keywords: Halopyridinylboronic acid Halogen ortho-directing Synthesis Lithium diisopropylamide
CLC: O627.8
Type: Master's thesis
Year: 2012
Downloads: 112
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Abstract


Halopyridinylboronic acids are halogen-substituted pyridinylboronic acids containing chloride, bromine, fluorine and other halogen atoms. Halopyridinylboronic acids have become important organic synthetic intermediates, widely used in pharmceutital and pesticide active compound. Saccharide sensors and functional materials are also very impartant to use. In this dissertation, the synthetic optimizations of monohalopyridinylboronic and dihalopyridinylboronic acids were studied in detail.Utilizing the halogen as an ortho-directing group, monohalopyridinylboronic and dihalopyridinylboronic acids, such as 2-bromopyridinc-3-boronic acid, 3-chloropyridine-4-boronic acid,2,6-dichloropyridine-3-boronic acid and 5-bromo-2-fluoropyridine-3-boronic acid, were synthesized with lithium diisopropylamide (LDA). The effects on yield were analyzed with parallel contrast experiments, and the optimized process parameters were obtained as follows:2-Bromopyridine-3-boronic acid:the optimized reactant molar ratio of 2-bromopyridine, LDA and trimethyl borate is 1:1.2:1.2 under lithiation temperature (-60℃) and lithiation time (0.75 h).3-Chloropyridine-4-boronic acid:the reactant molar ratio of 3-chloropyridine, LDA, trimethyl borate is 1:1.2:1.2 under lithiation temperature (-70℃) and lithiation time (0.5 h).2,6-Dichloropyridine-3-boronic acid:the reactant molar ratio of 2,6-dichloropyridine, LDA and trimethyl borate is 1:1.2:1.2 under lithiation temperature (-30℃) and lithiation time (2 h).5-Bromo-2-fluoropyridinc-3-boronic acid:the reactant molar ratio of 5-bromo-2-fluoropyridine, LDA, trimethyl borate is 1:1.2:1.2 under lithiation temperature (-30℃) and lithiation time (1 h).

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Elements in organic compounds > Ⅷ of group elements, organic compounds
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