期刊
TETRAHEDRON LETTERS
卷 52, 期 1, 页码 13-16出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.133
关键词
Hexabromoacetone; Benzyl bromides; Benzyl alcohols; Drug intermediates
资金
- Saint Mary's College
- Van Smith family
- Center for Academic Innovation
- Department of Chemistry and Physics at Saint Mary's College, Notre Dame, IN
A series of benzyl bromides were efficiently prepared from the corresponding alcohols with Br3CCOCBr3/PPh3 at low temperatures and under neutral conditions. The present protocol was applied to the heterocyclic analogues and to the successful synthesis of the precursor of the antiulcer drug omeprazole, thus furnishing an alternate, mild method for the preparation of these drug intermediates. A significant steric factor was observed throughout both series supporting a S(N)2 mechanism. (C) 2010 Elsevier Ltd. All rights reserved.
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