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Synthesis 2012; 44(8): 1208-1212
DOI: 10.1055/s-0031-1290768
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phloroglucinol Monoaryl Ethers

Alexander M. Sherwood
Department of Chemistry, University of New Orleans,, New Orleans, LA 70148, USA, Fax: +1(504)2806860   Email: mtrudell@uno.edu
,
David M. Pond
Department of Chemistry, University of New Orleans,, New Orleans, LA 70148, USA, Fax: +1(504)2806860   Email: mtrudell@uno.edu
,
Mark L. Trudell*
Department of Chemistry, University of New Orleans,, New Orleans, LA 70148, USA, Fax: +1(504)2806860   Email: mtrudell@uno.edu
› Author Affiliations
Further Information

Publication History

Received: 13 January 2012

Accepted after revision: 21 February 2012

Publication Date:
27 March 2012 (online)

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Abstract

A variety of novel functionalized phloroglucinol mono­aryl ethers have been synthesized using a two-step procedure. Target ethers were synthesized by coupling electron-deficient aryl fluorides with 3,5-dimethoxyphenol via nucleophilic aromatic substitution (SNAr) in N-methylpyrrolidone and cesium carbonate. Subsequent boron tribromide-mediated demethylation gave a series of phloroglucinol monoaryl ethers in good overall yields.

Key words

arylation - ethers - nucleophilic aromatic substitution - phenols - phloroglucinol
 

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