تفاعل #1148668

معادلة التفاعل

2-bromoindene

t-Butyllithium

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

Magnesium bromide

→

product

المردود 70.0%

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

المردود 70.0%

المذيبات

ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر