Reaktion #1061249

Reaktionsgleichung

2-mercaptobiphenyl

sodium hydride

perfluoropropyl iodide

→

2-(heptafluoropropylthio)biphenyl

Ausbeute 87.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas slowly elevated to room temperature
2. 2
   workup.STIRRINGthe mixture was stirred for 2 days
3. 3
   SonstigeThe white precipitate formed in the reaction solution
4. 4
   Sonstigewas removed by filtration
5. 5
   Extraktionthe mixture was extracted with hexane
6. 6
   WaschenThe organic layer was washed with water
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   EinengenThe filtrate was concentrated under reduced pressure
10. 10
    Sonstigeto give a brown oil
11. 11
    SonstigeIt was purified by silica gel column chromatography (ethyl acetate:hexane=1:30)

Vorschrift

To a solution composed of 20 ml of DMF and 2.24 g (12 mmol) of 2-mercaptobiphenyl was added 481 mg (12 mmol) of sodium hydride (60% in oil) little by little under ice cooling and stirring. Then, 1.73 ml (12 mmol) of perfluoropropyl iodide was added dropwise. The temperature of the mixture was slowly elevated to room temperature, and the mixture was stirred for 2 days. The white precipitate formed in the reaction solution was removed by filtration. Water was addd to the filtrate, and the mixture was extracted with hexane. The organic layer was washed with water, 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 (ethyl acetate:hexane=1:30) to give 3.46 g (87.3%) of 2-(heptafluoropropylthio)biphenyl as a colorless oil. The properties of the product were as shown below.

Quelle