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

HRID 1391860
Notes
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Reaction equation

HRID 1391860 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7854
Propionitrile
Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f39b7ab45c3b427a8aac35458b2c090d
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07339082B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes