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Water → {4-(Pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}(triflyl)methane

HRID 1391860
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1391860
Br[CH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([C:11]2[C:16]([F:17])=[C:15]([F:18])[C:14]([F:19])=[C:13]([F:20])[C:12]=2[F:21])=[C:5]([F:22])[C:4]=1[F:23].[F:24][C:25]([F:30])([F:29])[S:26]([O-:28])=[O:27].[Na+].O.C(OCC)(=O)C>C(#N)CC>[F:17][C:16]1[C:11]([C:6]2[C:7]([F:10])=[C:8]([F:9])[C:3]([CH2:2][S:26]([C:25]([F:30])([F:29])[F:24])(=[O:28])=[O:27])=[C:4]([F:23])[C:5]=2[F:22])=[C:12]([F:21])[C:13]([F:20])=[C:14]([F:19])[C:15]=1[F:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23690734Sodium trifluoromethanesulfinateHCID 865911214-Bromomethylperfluorobiphenyl

Produkt 1

HCID 22186455{4-(Pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}(triflyl)methaneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7854
Propionitrile
Lösungsmittel

Versuchsvorschrift

4-bromomethylperfluorobiphenyl (3.68 g, 9 mmol) and sodium trifluoromethane sulfinate (1.69 g, 10.8 mmol) were dissolved in propionitrile (30 mL), and the resultant solution was subjected to heating under reflux for 12 hours. After the reaction, the solution was cooled to room temperature, and water was added for extraction with ethyl acetate. The organic phase was dried with magnesium sulfate, filtrated, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (hexane-ethyl acetate=20:1 to 8:1 to 1:1), and the aimed {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}(triflyl)methane (3.91 g, 8.46 mmol, 94% yield) was isolated. 1H NMR (CDCl3, 300 MHz) δ 4.75 (s, 2H, CH2Tf); 19F NMR (CDCl3, 282 MHz) δ−78.24 (s, 3F, CF3), −136.82 to −136.62 (m, 1F), −137.72 (dd, J=10.7, 18.3 Hz, 2F), −138.84 (dd, J=10.7, 18.3 Hz, 2F), −149.69 (t, J=21.3 Hz, 1F), −160.63 (dt, J=6.1, 21.3 Hz, 2F).

Aufarbeitung

  1. temperatureto heating
  2. temperatureunder reflux for 12 hours
  3. customAfter the reaction
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltrated
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography (hexane-ethyl acetate=20:1 to 8:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f39b7ab45c3b427a8aac35458b2c090d
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07339082B2

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