Synthesis 2010(24): 4268-4272  
DOI: 10.1055/s-0030-1258965
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Hydroxylation of Aryl Halides with Tetrabutylammonium Hydroxide: Synthesis of Substituted Phenols and Alkyl Aryl Ethers

Rajesh Paul, Md Ashif Ali, Tharmalingam Punniyamurthy*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
Fax: +91(361)2690762; e-Mail: tpunni@iitg.ernet.in;
Further Information

Publication History

Received 19 July 2010
Publication Date:
09 November 2010 (online)

Abstract

The selective hydroxylation of aryl iodides and aryl bromides with tetrabutylammonium hydroxide pentahydrate is described. For this, the combination of copper(I) iodide and 8-hydroxyquinaldine at 70-130 ˚C in a mixture of dimethyl sulfoxide and water (2:3) is used. The resultant phenols can be readily reacted with alkyl and allyl halides in situ to provide the corresponding alkyl or allyl aryl ethers in high yields. The reactions are simple, general, and efficient, affording substituted phenols and alkyl aryl ethers under aerobic conditions.

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