Reaktion #466519

Reaktionsgleichung

ammonium chloride

3-(2-bromoethyl)-2-methylindene

2,7-di-t-butylfluorene

n-butyllithium

→

aimed product

Ausbeute 93.1%

1-(2,7-di-t-butyl-9-fluorenyl)-2-(2-methyl-1-indenyl)ethylene

Ausbeute 93.1%

Lösungsmittel

ether

ether

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 100 ml four-necked flask equipped with a reflux tube
2. 2
   SonstigeThe reaction liquid
3. 3
   workup.ADDITIONwas dropwise added over a period of 30 minutes
4. 4
   Sonstigeto spontaneously rise to room temperature
5. 5
   workup.STIRRINGby stirring for 15 hours
6. 6
   Sonstigeto separate an ether phase
7. 7
   ExtraktionThe aqueous phase was extracted with ether (100 ml×2)
8. 8
   Trocknena combined organic phase was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    Filtrationfiltrated

Vorschrift

To a 100 ml four-necked flask equipped with a reflux tube, a thermometer and a dropping funnel, 2,7-di-t-butylfluorene (1.18 g, 4.22 mmol) and dehydrated ether (30 ml) were introduced. To the flask was dropwise added a hexane solution of n-butyllithium (1.67 mol/l, 2.8 ml, 4.64 mmol) at 0° C. over a period of 1 hour, followed by stirring at room temperature for 7 hours. The reaction liquid became red orange transparent. Then, the liquid was cooled to −78° C. (a yellow orange slurry), to which a solution of 3-(2-bromoethyl)-2-methylindene (1 g, 4.22 mmol) in dehydrated ether (10 ml) was dropwise added over a period of 30 minutes. Then, the temperature of the system was allowed to spontaneously rise to room temperature, followed by stirring for 15 hours. The reaction mixture gradually became a yellow slurry. The resulting yellow slurry was poured into 200 ml of a saturated ammonium chloride aqueous solution to separate an ether phase. The aqueous phase was extracted with ether (100 ml×2), and a combined organic phase was dried over anhydrous magnesium sulfate, Then, the solvent was distilled off, and the resulting white yellow powder was reslurried with hexane (100 ml) and filtrated to obtain 1.70 g (yield: 93%) of an aimed product of a white powder.

Quelle