Reaktion #1104324

Reaktionsgleichung

2-bromoindene

t-Butyllithium

1-Bromo-3.5-di-t-butylbenzene

Magnesium bromide

→

product

Ausbeute 70.0%

2-(3,5-Di-t-butylphenyl)indene

Ausbeute 70.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at −70° C. over a two-hour period
2. 2
   TemperaturThe mixture was then cooled to 5° C.
3. 3
   TemperaturThe mixture was warmed to room temperature
4. 4
   Temperaturrefluxed for three hours
5. 5
   TemperaturThe solution was cooled to room temperature
6. 6
   Sonstigethe reaction was quenched carefully with water
7. 7
   SonstigeThe layers were separated
8. 8
   Waschenthe organics washed with salt brine
9. 9
   Trocknendried over magnesium sulfate
10. 10
    SonstigeThe solvents were evaporated
11. 11
    workup.DISTILLATIONthe product was distilled twice
12. 12
    Sonstigerecrystallized from hexane

Vorschrift

1-Bromo-3.5-di-t-butylbenzene (47.2 g, 0.175 mol) was dissolved in ether (500 mL) and cooled to −70° C. t-Butyllithium (200 mL of 1.7 M solution in pentane, 0.34 mol) was added at −70° C. over a two-hour period. The solution was allowed to warm to room temperature slowly. Magnesium bromide etherate (46.5 g. 0.18 mol) was added and the slurry was stirred for one hour. The mixture was then cooled to 5° C. and 2-bromoindene (34.2 g, 0.18 mol) was added. The mixture was warmed to room temperature and then refluxed for three hours. The solution was cooled to room temperature and the reaction was quenched carefully with water. The layers were separated and the organics washed with salt brine and dried over magnesium sulfate. The solvents were evaporated and the product was distilled twice and recrystallized from hexane to give 37.1 g of product (70% yield).

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