Réaction #498996

Équation de réaction

2-bromoindene

t-Butyllithium

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

Magnesium bromide

→

product

Rendement 70.0%

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

Rendement 70.0%

Solvants

ether

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source