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Zur Synthese sulfonierter Derivate von 4-Fluoranilin

✍ Scribed by Alfred Courtin


Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
339 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis


Syntheses of Sulfonated Derivatives of 4‐Fluoroaniline

Synthesis of 2‐amino‐5‐fluorobenzenesulfonic acid (2) was achieved by baking the hydrogen sulfate of 4‐fluoroaniline (1). Sulfonation of p‐fluoroacetanilide (4) with oleum followed by hydrolysis gave 5‐amino‐2‐fluorobenzenesulfonic acid (3). The same reaction with 1 yielded 3 in an impure state. The structures of 2 and 3 were confirmed by converting the diazonium chlorides derived from 5‐fluoro‐2‐nitroaniline (5) and from 2‐fluofo‐5‐nitroaniline (8) to 5‐fluoro‐2‐nitrobenzene‐sulfonyl chloride (6) and 2‐fluoro‐5‐nitrobenzenesulfonyl chloride (9), respectively, followed by hydrolysis of 6 to 5‐fluoro‐2‐nitrobenzenesulfonic acid (7), and of 9 to 2‐fluoro‐5‐nitrobenzenesulfonic acid (10), and by final reduction. Compound 10 was also obtained by sulfonation of 1‐fluoro‐4‐nitrobenzene (11) with oleum.


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