Reaktion #1999350

Reaktionsgleichung

m-toluidine

tri(tert-butyl)phosphine

9-(3-bromophenyl)-9-phenylfluorene

sodium tert-butoxide

→

white solid

Ausbeute 82.0%

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 placed
2. 2
   Sonstigewas set to 60° C.
3. 3
   FiltrationAfter that, 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
4. 4
   Sonstigeto give a filtrate
5. 5
   SonstigeA solid obtained by concentration of the obtained filtrate
6. 6
   Sonstigewas purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene
7. 7
   Sonstigerecrystallized from a mixed solvent of toluene and hexane

Vorschrift

Into a 200 mL three-neck flask were placed 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 this mixture was raised to 80° C., and the mixture was stirred for 2.0 hours. After that, 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. A solid obtained by concentration of the obtained filtrate was purified by silica gel column chromatography (a developing solvent in which the ratio of hexane to toluene was 1:1) and recrystallized from a mixed solvent of toluene and hexane. Accordingly, 2.8 g of a white solid of the object of the synthesis was obtained in 82% yield. The synthesis scheme of Step 1 above is illustrated in the following scheme (J-1).

Quelle