반응 #1148671

반응 방정식

n-butyl lithium

1,3,5-Tribromobenzene

n-Butyllithium

trimethylchlorosilane

trimethylchlorosilane

→

colorless liquid

수율 141.4%

3,5-Bis(trimethylsilyl)bromobenzene

수율 141.4%

용매

diethylether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise over a one-hour period
2. 2
   기타near −70° C
3. 3
   온도warmed to −10 C
4. 4
   workup.WAITover a two-hour period
5. 5
   기타was then recooled to −70° C.
6. 6
   workup.STIRRINGto stir
7. 7
   온도warm to room temperature overnight
8. 8
   온도The solution was cooled to −70° C.
9. 9
   workup.STIRRINGThe resulting slurry was stirred for one hour at −70° C.
10. 10
    온도warmed to −10° C. over a two-hour period
11. 11
    기타recooled to −70° C
12. 12
    온도to warm to room temperature overnight
13. 13
    기타The mixture was quenched with water
14. 14
    기타the layers were separated
15. 15
    세척The organic layer was washed twice with sodium bicarbonate solution and with salt brine
16. 16
    건조then dried over magnesium sulfate
17. 17
    기타The solvents were evaporated under vacuum
18. 18
    workup.DISTILLATIONthe product distilled twice under vacuum

실험 절차

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.

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