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Molbank 2009, 2009(3), M602; doi:10.3390/M602

Preparation of 5-Bromo-2-naphthol: The Use of a Sulfonic Acid as a Protecting and Activating Group

Department of Chemistry, College of William and Mary, Williamsburg, VA 23187, USA
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Received: 2 June 2009 / Accepted: 25 June 2009 / Published: 29 June 2009
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Abstract

The preparation of 5-bromo-2-naphthol (4) in three steps from 5-amino-2-naphthol (1) is described. A sulfonic acid group is introduced at the 1-position as an activating and protecting group for the Sandmeyer reaction. The sulfonate group allows for the use of only water and sulfuric acid as solvents. The sulfonic acid is introduced with three equivalents of sulfuric acid, and it is removed in 20% aq. sulfuric acid.
Keywords: Sandmeyer reaction; protecting group; sulfonation; desulfonation Sandmeyer reaction; protecting group; sulfonation; desulfonation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Everett, R.; Hamilton, J.; Abelt, C. Preparation of 5-Bromo-2-naphthol: The Use of a Sulfonic Acid as a Protecting and Activating Group. Molbank 2009, 2009, M602.

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