Syntheses of Sulfonated Derivatives of 2‐Fluoroaniline Synthesis of 4‐amino‐3‐fluorobenzenesulfonic acid (**3**) was achieved in two ways: reaction of 2‐fluoroaniline (**1**) with amidosulfonic acid and by first conventionally converting 4‐nitro‐3‐fluoroaniline (**8**) to 4‐nitro‐3‐fluorobenzenesul
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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