تفاعل #8644

معادلة التفاعل

hexabromospirobifluorene

biphenylboronic acid

→

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

المذيبات

toluene

toluene

potassium carbonate

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a 250 ml two-necked flask fitted
2. 2
   درجة الحرارةwith reflux condenser and precision glass stirrer
3. 3
   درجة الحرارةThe mixture is refluxed under nitrogen
4. 4
   درجة الحرارةunder reflux for 7 hours
5. 5
   ترشيحthe cooled solution is filtered
6. 6
   استخلاصthe filtrate is extracted twice
7. 7
   workup.STIRRINGby shaking with water (
8. 8
   أخرىthe phase separation, chloroform
9. 9
   workup.ADDITIONis added)
10. 10
    تجفيفThe organic phase is dried over sodium sulfate
11. 11
    ترشيحfiltered through a short column of silica gel
12. 12
    أخرىsubsequently evaporated on a rotary evaporator
13. 13
    أخرىThe product is further purified by recrystallization from dichloromethane/pentane

الإجراء التجريبي

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.

المصدر