The Synthesis of 3-Methoxycarbonylbenzofuran-2(3H)-one Derivatives via Copper(I)-Catalyzed Coupling of o-Bromophenols with Dimethyl Malonate

Howard C. Hang; Elizabeth Drotleff; Gregory I. Elliot; Todd A. Ritsema; Joseph P. Konopelski

doi:10.1055/s-1999-3401

Synthesis 1999; 1999(3): 398-400
DOI: 10.1055/s-1999-3401

short paper

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The Synthesis of 3-Methoxycarbonylbenzofuran-2(3H)-one Derivatives via Copper(I)-Catalyzed Coupling of o-Bromophenols with Dimethyl Malonate

Howard C. Hang^* , Elizabeth Drotleff, Gregory I. Elliot, Todd A. Ritsema, Joseph P. Konopelski

^*Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA; Fax +1(8 31)4 59 29 35; E-mail: joek@chemistry.ucsc.edu

Abstract

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The preparation of benzofuran-2(3H)-ones via the copper(I)-catalyzed reaction between dialkyl malonates and o-halophenols has been investigated. It was shown that the reaction is catalytic in the copper(I) source, with CuBr the most effective reagent. In addition, significant increases in yield can be achieved through the isolation of the corresponding sodium salt of the benzofuranone product. These salts are air stable solids that do not decompose over a period of several months and are not hygroscopic.

antitumor compounds - benzofuranone - phenols - copper catalysis

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