Reacción #1148668

Ecuación de reacción

2-bromoindene

t-Butyllithium

1-Bromo-3,5-di-t-butylbenzene

Magnesium bromide

→

product

Rendimiento 70.0%

2-(3,5-di-t-Butylphenyl)indene

Rendimiento 70.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente