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31.1.1.5.2.1 Variation 1: Reaction with Hydrogen Fluoride

DOI: 10.1055/sos-SD-031-00002

Sandford, G.Science of Synthesis, (20073157.

Mixtures of sodium nitrite and either aqueous or anhydrous hydrogen fluoride can be used for a one-pot transformation of aniline derivatives 50 into fluoroarene products 51 (Scheme 27).[‌136‌] Reactions performed using aqueous hydrogen fluoride are generally low yielding, with some exceptions, so anhydrous hydrogen fluoride is more commonly used as both the reagent and reaction medium. One-pot fluorodediazoniation by anhydrous hydrogen fluoride is used on a large scale for the industrial synthesis of fluorobenzene, fluorotoluenes,[‌137‌] and various other fluoroarenes.

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