2,3,4,6-Tetrafluoronitrobenzene

Chemical Properties

yellow liquid

Uses

Molluscicidal activity of 2,3,4,6-tetrafluoronitrobenzene against Biomphalaria glabrata has been investigated. Palladium-catalyzed cross-coupling reactions of 2,3,4,6-tetrafluoronitrobenzene with alkyne derivatives has been studied. Reaction of 2,3,4,6-tetrafluoronitrobenzene with 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene in the presence of water molecules in acetonitrile has been investigated.

General Description

Molluscicidal activity of 2,3,4,6-tetrafluoronitrobenzene against Biomphalaria glabrata has been investigated. Palladium-catalyzed cross-coupling reactions of 2,3,4,6-tetrafluoronitrobenzene with alkyne derivatives has been studied. Reaction of 2,3,4,6-tetrafluoronitrobenzene with 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene in the presence of water molecules in acetonitrile has been investigated.

Synthesis

For the large-scale synthesis of 1,2,3,5-tetrafluoro-4-nitrobenzene, a mixed solution of concentrated nitric acid (990 g) in concentrated sulfuric acid (973 mL) was first pre-cooled, and then the mixed solution was slowly added to a cold solution of 1,2,3,5-tetrafluorobenzene (973.1 g) dissolved in concentrated sulfuric acid (2,920 mL) at temperatures ranging from 0 °C to 10 °C, with the addition process being controlled to be completed within 1.5 The addition process was completed within 1.5 hours. After the addition was completed, the reaction temperature was maintained between 0 °C and 10 °C, and the yellow reaction solution was continued to be stirred for 1 hour until the analysis confirmed the completion of the reaction. Subsequently, the reaction solution was slowly poured into water (9730 g) that had been pre-cooled to below 25 °C, and dichloromethane (9730 mL) was added for extraction. After separation of the organic phase, it was washed twice with deionized water (10 L). The dichloromethane layer was concentrated to give a yellow oil. Finally, the oily substance was distilled under reduced pressure (2.5 mbar) at 70 °C to 75 °C to give a yellow oily product with 98% purity and 72.4% yield.

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 22, p. 7348 - 7350
[2] Patent: US2012/316149, 2012, A1. Location in patent: Page/Page column 11
[3] Patent: WO2012/168884, 2012, A1. Location in patent: Page/Page column 26; 27
[4] Russian Chemical Bulletin, 1998, vol. 47, # 5, p. 924 - 927
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 153