Reaktion #326386

Reaktionsgleichung

3,5-dimethylaniline

9-(4-bromophenyl)-9-phenylfluorene

sodium tert-butoxide

tri(tert-butyl)phosphine

→

white solid

Ausbeute 92.9%

3,5-dimethylphenyl-4-(9-phenyl-9H-fluoren-9-yl)phenylamine

Ausbeute 92.9%

Lösungsmittel

toluene

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 200 mL three-neck flask were put
2. 2
   Sonstigewas set to 60° C.
3. 3
   workup.STIRRINGwas then stirred for 4.5 hours
4. 4
   FiltrationAfter the stirring, the mixture was suction-filtered through Florisil, Celite, and alumina
5. 5
   Sonstigeto give a filtrate
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigeto give a solid, which
8. 8
   Sonstigewas then purified by silica gel column chromatography (the developing solvent
9. 9
   Sonstigeto give a while solid
10. 10
    SonstigeRecrystallization of the obtained white solid from toluene and hexane

Vorschrift

In a 200 mL three-neck flask were put 3.6 g (9.1 mmol) of 9-(4-bromophenyl)-9-phenylfluorene and 2.7 g (27.7 mmol) of sodium tert-butoxide. The air in the flask was replaced with nitrogen. To this mixture were added 46.0 mL of toluene and 1.2 mL (9.6 mmol) of 3,5-dimethylaniline. The temperature of this mixture was set to 60° C., and 53.2 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. The temperature of the mixture was raised to 80° C., followed by stirring for 0.5 hours. Then, 0.30 mL of a 10% hexane solution of tri(tert-butyl)phosphine was added to the mixture, which was then stirred for 4.5 hours. After the stirring, the mixture was suction-filtered through Florisil, Celite, and alumina to give a filtrate. The filtrate was concentrated to give a solid, which was then purified by silica gel column chromatography (the developing solvent has a 1:1 ratio of hexane to toluene) to give a while solid. Recrystallization of the obtained white solid from toluene and hexane gave 3.7 g of a white solid in 92% yield, which was the substance to be produced. The synthesis scheme of this Step 1 is shown in the following (E9-1).

Quelle