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DOI: 10.1055/s-0029-1219548
An Efficient Synthesis of Phenol via CuI/8-Hydroxyquinoline-Catalyzed Hydroxylation of Aryl Halides and Potassium Hydroxide
Publication History
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
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
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.