Preparation of 4-Azido-2,6-diflurophenol Acetate, a Click Reagent

The title compound was prepared from 2,6-difluorophenol in four steps. Acetylation, followed by nitration, reduction to the amine and diazotization/azide formation proceeded in the expected fashion. A copper-catalyzed Huisgen cyclization between the compound and phenylacetylene was carried out as a model and the triazole isolated. The propargyl ester of naproxen was prepared (naproxen/propargyl alcohol/carbodiimide) and the subsequent click reaction carried out. It is expected that this strategy will afford access to materials with dual biological activity.