Reaktion #2001577

Reaktionsgleichung

1-bromopyrene

4-methylphenylboronic acid

tripotassium phosphate

dimethylformamide

→

1-(4-methylphenyl)pyrene

Ausbeute 85.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to room temperature
2. 2
   workup.STIRRINGby stirring at room temperature for 0.5 hours
3. 3
   FiltrationThe precipitated solid was collected by filtration
4. 4
   Waschenwashed twice with 200 ml of water
5. 5
   workup.DISSOLUTIONThe resulting solid was dissolved in 500 ml of dichloromethane
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered through Celite
8. 8
   SonstigeThe filtrate was evaporated
9. 9
   Waschenthe residue was washed twice with 200 ml of methanol
10. 10
    Filtrationthe precipitated solid was collected by filtration
11. 11
    Sonstigevacuum-dried

Vorschrift

A mixed solution of 45.0 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34.0 g of tripotassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate and 1.6 L of dimethylformamide was heated and stirred under a nitrogen gas stream at 120° C. for 5 hours. The solution was cooled to room temperature and 1.6 L of water was poured into the solution, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 200 ml of water. The resulting solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol, and then the precipitated solid was collected by filtration and vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene.

Quelle