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

HRID 459436
Notes
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Reaction equation

HRID 459436 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.

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-0e51210971dc458bb57d161ed8d10517
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07193113B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes