Reaktion #70667

Reaktionsgleichung

2,7-dibromofluorene

N-phenyl-1-naphthylamine

→

N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was purged with a strong nitrogen flow for 30 minutes
2. 2
   workup.ADDITIONfollowed by the addition of sodium tert-butoxide (44.5 g) by funnel
3. 3
   workup.ADDITIONTris(dibenzylideneacetone)dipalladium(0) (5.65 g) was added to the reaction
4. 4
   workup.ADDITIONTri-tert-butyl phosphine (3.75 g) in anhydrous toluene (20 mL) was added via syringe
5. 5
   TemperaturThe reaction was heated
6. 6
   Temperaturto reflux for 2 hours
7. 7
   Sonstigereaction completion
8. 8
   SonstigeThe vessel was removed
9. 9
   Temperaturfrom heat
10. 10
    FiltrationThe reaction solution was filtered through a celite/silica gel plug and solvent
11. 11
    Sonstigewas then removed by rotary evaporation
12. 12
    SonstigeThe crude material was initially purified by flash chromatography
13. 13
    Sonstigeto yield NMR pure product

Vorschrift

To a 2-liter three-neck round bottom flask was added anhydrous toluene (1000 mL) by cannula. 2,7-dibromofluorene (50.0 g) was added to this flask, then stirred until all dissolved. N-phenyl-1-naphthylamine (81.14 g) was then added. The reaction vessel was purged with a strong nitrogen flow for 30 minutes, followed by the addition of sodium tert-butoxide (44.5 g) by funnel. Tris(dibenzylideneacetone)dipalladium(0) (5.65 g) was added to the reaction. Tri-tert-butyl phosphine (3.75 g) in anhydrous toluene (20 mL) was added via syringe. The reaction was heated to reflux for 2 hours and reaction completion was confirmed by thin-layer chromatography. The vessel was removed from heat and allowed to cool to room temperature. The reaction solution was filtered through a celite/silica gel plug and solvent was then removed by rotary evaporation. The crude material was initially purified by flash chromatography, followed by sublimation to yield NMR pure product.

Quelle