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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Novel Route to 2-Trifluoromethylated Benzofurans

, , &
Pages 716-732 | Received 24 Apr 2008, Published online: 28 Jan 2009
 

Abstract

A novel route for the synthesis of a variety of 2-trifluoromethylbenzofurans is reported. By selection of solvents, the key intermediates, 2-chloro-3,3,3-trifluoropropenyl phenyl acetates, were cyclized either to give 2-trifluoromethyl-substituted benzofurans or to yield trifluoromethyl modified o-alkynylphenols. The latter intermediates could also be cyclized to give 3-iodo-2-trifluoromethyl-substituted benzofurans.

ACKNOWLEDGMENTS

We thank the National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, for support of this research.

Notes

a Isolated yield.

b The values in bracket are Z/E ratio of 2.

a Reaction conditions: 2a (0.5 mmol) dissolved in 2 mL solvent, the base was added and the reaction was performed at room temperature.

b GC yield.

a Isolated yield.

a Isolated yield.

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