Reaktion #800762

Reaktionsgleichung

m-toluidine

tri(tert-butyl)phosphine

9-(3-bromophenyl)-9-phenylfluorene

sodium tert-butoxide

→

3-methylphenyl-3-(9-phenyl-9H-fluoren-9-yl)phenylamine

Ausbeute 82.0%

Lösungsmittel

hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 200-mL three-neck flask were put
2. 2
   Sonstigewas set to 60° C.
3. 3
   FiltrationAfter the stirring, suction filtration
4. 4
   Sonstigeto obtain a filtrate
5. 5
   EinengenThe filtrate was concentrated
6. 6
   Sonstigeto give a solid, which
7. 7
   Sonstigewas then purified by silica gel column chromatography
8. 8
   Sonstigein a ratio of 1:1, and recrystallization with a mixed solvent of toluene and hexane
9. 9
   Sonstigewas obtained in 82% yield
10. 10
    SonstigeA synthesis scheme (z-1) of Step 1

Vorschrift

Into a 200-mL three-neck flask were put 3.2 g (8.1 mmol) of 9-(3-bromophenyl)-9-phenylfluorene and 2.3 g (24.1 mmol) of sodium tert-butoxide, and the air in the flask was replaced with nitrogen. To this mixture were added 40.0 mL of toluene, 0.9 mL (8.3 mmol) of m-toluidine, and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The temperature of this mixture was set to 60° C., and 44.5 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 2.0 hours. After the stirring, suction filtration was carried out through Florisil, Celite, and alumina to obtain a filtrate. The filtrate was concentrated to give a solid, which was then purified by silica gel column chromatography using hexane and toluene as a developing solvent in a ratio of 1:1, and recrystallization with a mixed solvent of toluene and hexane was performed, so that 2.8 g of a white solid was obtained in 82% yield. A synthesis scheme (z-1) of Step 1 is shown below.

Quelle