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Authors: Effenberger, Franz
Streicher, Willi
Title: Darstellung aromatischer Fluor-Verbindungen durch nucleophilen Austausch von Nitro-Gruppen gegen Fluorid
Other Titles: Synthesis of aromatic fluoro compounds by nucleophilic exchange of nitro groups by fluoride
Issue Date: 1991 Zeitschriftenartikel Chemische Berichte 124 (1991), S. 157-162. URL
Abstract: Da wir an der Herstellung speziell substituierter Fluoraromaten interessiert waren, haben wir den nucleophilen Austausch von Nitrit gegen Fluorid in Aromaten grundlegend untersucht.
The synthesis of aromatic fluoro compounds from the respective nitro compounds by nucleophilic substitution of nitrite by fluoride is described. Reasonable yields in case of nonactivated nitro compounds are only obtained if the nitrite formed in the reaction is eliminated by acylation. 1-Fluoro-3-nitrobenzene (2) was obtained from 1,3-dinitrobenzene (1), and 1-fluoro-3,5-dinitrobenzene (9) as well as 1,3-difluoro-5-nitrobenzene (10) from 1,3,5-trinitrobenzene (8) in yields up to 92% by reaction of nitro compounds with potassium fluoride in sulfolane at 180 - 200°C in the presence of phthaloyl dichloride (6); 1,2-difluoro-4-nitrobenzene (12) was formed in 58% yield from 2,4-dinitro-1-fluorobenzene (11) in the presence of pyromellitoyl tetrachloride (13).
Appears in Collections:03 Fakultät Chemie

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