Reaktion #1114503

Reaktionsgleichung

1-bromopyrene

4-methylphenylboronic acid

tripotassium phosphate

dimethylformamide

→

1-(4-methylphenyl)pyrene

Ausbeute 85.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling 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 resultant solid was dissolved in 500 ml of dichloromethane
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe filtrate was evaporated
10. 10
    Waschenthe residue was washed twice with 200 ml of methanol
11. 11
    FiltrationThe precipitated solid was collected by filtration
12. 12
    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 with stirring under a nitrogen gas flow at 120° C. for 5 hours. After cooling to room temperature, 1.6 L of water was injected, 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 resultant solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol. The precipitated solid was collected by filtration and then vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene.

Quelle