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Synfacts 2006(4): 0338-0338  
DOI: 10.1055/s-2006-932066
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of Polymerizable Heterofluorene Derivatives

Contributor(s): Timothy M. Swager, Mark S. Taylor
R.-F. Chen, Q.-L. Fan, C. Zheng, W. Huang*
Fudan University, Shanghai, P. R. of China
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

An efficient synthetic sequence for the preparation of diiodo-dibromobiaryl 1 is described. This method enables the preparation of multigram quantities of 1 from o-dianisidine, an inexpensive starting material. Selective lithium-iodine exchange and quenching with silicon-, germanium-, boron- and phosphorus-based electrophiles results in the formation of 2,7-dibromo-9-heterofluorenes in modest yields.