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Synlett 2010(6): 976-978  
DOI: 10.1055/s-0029-1219548
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Phenol via CuI/8-Hydroxyquinoline-Catalyzed Hydroxylation of Aryl Halides and Potassium Hydroxide

Stefan Maurera, Wei Liub, Xiaojing Zhangb, Yongwen Jiang*a, Dawei Ma*a
a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200062, P. R. of China
Fax: +86(21)64166128; e-Mail: jiangyw@mail.sioc.ac.cn; e-Mail: madw@mail.sioc.ac.cn;
b Shenyang Pharmaceutical University, 103 Wenhua Lu, Shenyang 110016, P. R. of China
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Publication History

Received 14 December 2009
Publication Date:
23 February 2010 (online)

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Abstract

The CuI/8-hydroxyquinoline-catalyzed direct hydroxylation of aryl iodides with KOH takes place at 100 ˚C in a mixed solvent system (t-BuOH-DMSO-H2O), providing the corresponding phenols in great diversity. Aryl bromides are found to be rather less reactive under these reaction conditions.

Key words

coupling - hydroxylation - 8-hydroxyquinoline - phenols

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Typical Procedure for Preparation of 2a An oven-dried Schlenk tube was charged with CuI (19 mg, 0.1 mmol), 4-iodoanisole (1 mmol), 8-hydroxyquinoline (29 mg, 0.2 mmol), and KOH (224 mg, 4 mmol). The tube was evacuated and backfilled with argon, and DMSO (1 mL), t-BuOH (1 mL), and H2O (0.1 mL) were added. The reaction mixture was stirred at 100 ˚C till the material was completely converted (monitored by TLC). Then the mixture was acidified to pH ˜1 with 1 N HCl. Extract workup followed by chromatography afford 4-methoxy-phenol in 96% yield.