Dimethylformamide → 2-(Perfluorooctylthio)biphenyl

HRID 974068

Reaction equation

HRID 974068 reaction equation
CN(C=O)C.[SH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[F:21][C:22](I)([F:45])[C:23]([F:44])([F:43])[C:24]([F:42])([F:41])[C:25]([F:40])([F:39])[C:26]([F:38])([F:37])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30]>O>[F:45][C:22]([F:21])([S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:23]([F:43])([F:44])[C:24]([F:41])([F:42])[C:25]([F:39])([F:40])[C:26]([F:37])([F:38])[C:27]([F:35])([F:36])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10491Perfluorooctyl iodideHCID 24758Sodium hydrideHCID 27604132-Phenylthiophenol

Product 1

HCID 156553492-(Perfluorooctylthio)biphenylYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution composed of 40 ml of DMF and 4.66 g (25 mmol) of 2-mercaptobiphenyl was added 1.00 g (25 mmol) of sodium hydride (60% in oil) little by little under ice cooling and stirring. Then, 13.6 g (25 mmol) of perfluorooctyl iodide was added. The temperature of the mixture was slowly elevated to room temperature, and the mixture was stirred for 2 hours. Water was addd to the reaction mixture, and the mixture was extracted with hexane. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give a brown oil. It was purified by silica gel column chromatography using hexane as an eluent to give 9.60 g (64%) of 2-(perfluorooctylthio)biphenyl as a colorless oil. The properties of the product were as shown below.

Workup

  1. customwas slowly elevated to room temperature
  2. stirringthe mixture was stirred for 2 hours
  3. extractionthe mixture was extracted with hexane
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a brown oil
  9. customIt was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-908ce0ba12bd4fb2ae01060942bb19b7
Source dataset
uspto-grants-1991_11
Patent number
US05066795

Linked notes

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