反応 #1148668

反応方程式

2-bromoindene

t-Butyllithium

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

Magnesium bromide

→

product

収率 70.0%

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

収率 70.0%

溶媒

ether

反応条件

後処理

1. 1
   workup.ADDITIONwas added at −70° C. over a two hour period
2. 2
   温度The mixture was then cooled to 5° C.
3. 3
   温度The mixture was warmed to room temperature
4. 4
   温度refluxed for three hours
5. 5
   温度The solution was cooled to room temperature
6. 6
   その他the reaction was quenched carefully with water
7. 7
   その他The layers were separated
8. 8
   洗浄the organics washed with salt brine
9. 9
   乾燥dried over magnesium sulfate
10. 10
    その他The solvents were evaporated
11. 11
    workup.DISTILLATIONthe product was distilled twice
12. 12
    その他recrystallized from hexane

実験手順

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%).

出典