Reaktion #1836114

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
   SonstigeIn a 200 mL three-neck flask were put
2. 2
   Sonstigewas set to 60° C.
3. 3
   Sonstigewas set to 80° C.
4. 4
   FiltrationAfter the stirring, the mixture was suction-filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), 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
   Sonstigerecrystallized with a mixed solvent of toluene and hexane
10. 10
    SonstigeAccordingly, 2.8 g of the target substance, white solid, was obtained in 82% yield
11. 11
    SonstigeThe synthesis scheme of this Step 1

Vorschrift

In 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. 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 set to 80° C., followed by stirring for 2.0 hours. After the stirring, the mixture was suction-filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), 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) and recrystallized with a mixed solvent of toluene and hexane. Accordingly, 2.8 g of the target substance, white solid, was obtained in 82% yield. The synthesis scheme of this Step 1 is shown in (J-1).

Quelle