반응 #1104324

반응 방정식

2-bromoindene

t-Butyllithium

1-Bromo-3.5-di-t-butylbenzene

Magnesium bromide

→

product

수율 70.0%

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

수율 70.0%

용매

ether

반응 조건

후처리

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

실험 절차

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).

출처