Preparation of 5-bromo-2-naphthol: The use of a sulfonic acid as a protecting and activating group

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. © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.