An Efficient K2CO3-Promoted Synthesis of 1-Bromo-2-aryloxyethane Derivatives and Evaluation of Larval Mortality against Aedes aegypti

Yina Pájaro,Ángel Sathicq,Esneyder Puello-Polo,Astrid Pérez,Jorge Trilleras,Gustavo Romanelli

doi:10.1155/2017/6175315

Abstract

The influences of reaction parameters on the etherification of phenols to obtain 1-bromo-2-aryloxyethane derivatives were evaluated. The compounds were prepared by direct etherification of phenols with 1,2-dibromoethane using anhydrous K2CO3 and acetonitrile as solvent reaction, at 80°C, in a reaction time of 6 h. Under these conditions, excellent yields (71%–94%) were obtained, with low yields of secondary products. The anhydrous K2CO3 was recycled by simple filtration, dried in vacuum, and reused. The compounds were characterized by conventional spectral data (MS and NMR). Larvicidal activity results showed a 100% larval mortality after 24-hour exposure to the compound 1-(2-bromoethoxy)-2-phenylbenzene.

Highlights

The synthesis of chemical compounds is associated with expensive and unfriendly environmental procedures. These disadvantages have become a challenge for chemists, transforming these methodologies into simple procedures, easy implementation, and low environmental impact, with the purpose of obtaining organic compounds with potential applications
All the products were identified by comparison of physical data with those reported or with those of authentic samples prepared by the respective conventional methods using sulfuric acid as catalyst
The structural diversity of phenolic derivatives commercially available makes them attractive substrates for the preparation of aryl alkyl ethers

Summary

Introduction

The synthesis of chemical compounds is associated with expensive and unfriendly environmental procedures These disadvantages have become a challenge for chemists, transforming these methodologies into simple procedures, easy implementation, and low environmental impact, with the purpose of obtaining organic compounds with potential applications. In this context, the synthesis of organic compounds including aromatic rings in their structure has been widely reported in the literature. The compounds with aromatic substructure have been reported to show a broad spectrum of pharmaceutical, agricultural, and chemical engineering applications and are scaffolding reagents for synthetic organic chemistry [1,2,3,4,5,6] They are ubiquitous structural units in biologically important molecules such as cyclooxygenase and β-galactosidase inhibitors and anticancer porphyrins [7]. A large number of them can be used as adhesives, herbicides, fungicides, and fire retardant [1, 8, 9]

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