反応 #1148671

反応方程式

n-butyl lithium

1,3,5-Tribromobenzene

n-Butyllithium

trimethylchlorosilane

trimethylchlorosilane

→

colorless liquid

収率 141.4%

3,5-Bis(trimethylsilyl)bromobenzene

収率 141.4%

溶媒

diethylether

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise over a one-hour period
2. 2
   その他near −70° C
3. 3
   温度warmed to −10 C
4. 4
   workup.WAITover a two-hour period
5. 5
   その他was then recooled to −70° C.
6. 6
   workup.STIRRINGto stir
7. 7
   温度warm to room temperature overnight
8. 8
   温度The solution was cooled to −70° C.
9. 9
   workup.STIRRINGThe resulting slurry was stirred for one hour at −70° C.
10. 10
    温度warmed to −10° C. over a two-hour period
11. 11
    その他recooled to −70° C
12. 12
    温度to warm to room temperature overnight
13. 13
    その他The mixture was quenched with water
14. 14
    その他the layers were separated
15. 15
    洗浄The organic layer was washed twice with sodium bicarbonate solution and with salt brine
16. 16
    乾燥then dried over magnesium sulfate
17. 17
    その他The solvents were evaporated under vacuum
18. 18
    workup.DISTILLATIONthe product distilled twice under vacuum

実験手順

1,3,5-Tribromobenzene (125 g, 0.4 mol), was dissolved in anhydrous diethylether (1 L), and cooled to −70° C. n-Butyllithium (250 mL, 1.6 M in hexanes, 0.4 mol) was added dropwise over a one-hour period keeping the temperature near −70° C. The solution was stirred for an additional 20 minutes at −70° C. and then warmed to −10 C. over a two-hour period. The solution was then recooled to −70° C. and trimethylchlorosilane (45 g, 0.4 mol) was added over a one hour period. The solution was allowed to stir and warm to room temperature overnight. The solution was cooled to −70° C. and an additional 0.4 mol n-butyl lithium was added over a one-hour period. The resulting slurry was stirred for one hour at −70° C., warmed to −10° C. over a two-hour period and then recooled to −70° C. An additional 0.4 mol of trimethylchlorosilane was added and the slurry was allowed to warm to room temperature overnight. The mixture was quenched with water and the layers were separated. The organic layer was washed twice with sodium bicarbonate solution and with salt brine then dried over magnesium sulfate. The solvents were evaporated under vacuum and the product distilled twice under vacuum to yield 85.2 g (70%) of a colorless liquid. b.p. 100-105° C. @ 0.5 mmHg.

出典