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• Hamilton, J
• Abelt, C
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• Hamilton, J
• Abelt, C
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• Hamilton, J
• Abelt, C

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

Short Note

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

Renata Everett, Jillian Hamilton and Christopher Abelt *

Department of Chemistry, College of William and Mary, Williamsburg, VA 23187, USA

* Author to whom correspondence should be addressed.

Received: 2 June 2009 / Accepted: 25 June 2009 / Published: 29 June 2009

Download PDF Full-Text [174 KB, uploaded 30 June 2009 03:03 CET]

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

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  m602.mol 3D structure (MOL, 1 KB) Display in MOL Viewer

  3D structure generated by CORINA by Molecular Networks.

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