反応 #8644

反応方程式

hexabromospirobifluorene

biphenylboronic acid

→

2,2′,4,4′,7,7′-hexabiphenylyl-9,9′-spirobifluorene

溶媒

toluene

toluene

potassium carbonate

反応条件

後処理

1. 1
   その他In a 250 ml two-necked flask fitted
2. 2
   温度with reflux condenser and precision glass stirrer
3. 3
   温度The mixture is refluxed under nitrogen
4. 4
   温度under reflux for 7 hours
5. 5
   ろ過the cooled solution is filtered
6. 6
   抽出the filtrate is extracted twice
7. 7
   workup.STIRRINGby shaking with water (
8. 8
   その他the phase separation, chloroform
9. 9
   workup.ADDITIONis added)
10. 10
    乾燥The organic phase is dried over sodium sulfate
11. 11
    ろ過filtered through a short column of silica gel
12. 12
    その他subsequently evaporated on a rotary evaporator
13. 13
    その他The product is further purified by recrystallization from dichloromethane/pentane

実験手順

In a 250 ml two-necked flask fitted with reflux condenser and precision glass stirrer, 1.6 g of hexabromospirobifluorene and 3 g of biphenylboronic acid are slurried in a mixture of 50 ml of toluene and 50 ml of 1 M potassium carbonate solution. The mixture is refluxed under nitrogen and 115 mg of tetrakis(triphenylphosphine)palladium in 5 ml of toluene are added. The mixture is boiled under reflux for 7 hours while stirring. After the reaction is complete, the cooled solution is filtered and the filtrate is extracted twice by shaking with water (to improve the phase separation, chloroform is added). The organic phase is dried over sodium sulfate, filtered through a short column of silica gel and subsequently evaporated on a rotary evaporator. The product is further purified by recrystallization from dichloromethane/pentane. This gives 2 g (80%) of colorless crystals which fluoresce blue under UV illumination.

出典