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Electrochemical fluorination of aromatic compounds in liquid R4NF · mHF—Part IV. fluorination of chlorobenzene

✍ Scribed by Kunitaka Momota; Hirohide Horio; Katsuya Kato; Masayuki Morita; Yoshiharu Matsuda

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
685 KB
Volume
40
Category
Article
ISSN
0013-4686

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✦ Synopsis

Electrochemical fluorination of chlorobenzene (1) in neat Et,NF mHF (Et = C,H, : m = 4.0, 4.45 and 4.7) was carried out on a platinum anode at 2.3 or 2.5 V vs. Ag/Ag' (0.01 M; M = mol dme3).

As the primary products, I-chloro-2-fluorobenzene (2) and 1-chloro-4-fluorobenzene (3) were obtained, whose molar ratio (Z/3) was about 1:3. The product 2 was further fluorinated to 1-chloro-3,6,6-trifluoro-1,4-cyclohexadiene (2a) with a high yield. On the other hand, the electrochemical fluorination of 3 yielded 3-chloro-3,6,6-trifluoro-1,4-cyclohexadiene (319, 2thloro-5,5,6-trifluoro-1,3-cyclohexadiene (3b) and 3,3,6, 6-tetrafluoro-1,Ccyclohexadiene (6a). A larger amount of 6 was obtained at the final stages of the electrolyses of 1 and 3. The yield of 6a varied with the electrolysis conditions.

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