تفاعل #1148671

معادلة التفاعل

n-butyl lithium

1,3,5-Tribromobenzene

n-Butyllithium

trimethylchlorosilane

trimethylchlorosilane

→

colorless liquid

المردود 141.4%

3,5-Bis(trimethylsilyl)bromobenzene

المردود 141.4%

المذيبات

diethylether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise over a one-hour period
2. 2
   أخرىnear −70° C
3. 3
   درجة الحرارةwarmed to −10 C
4. 4
   workup.WAITover a two-hour period
5. 5
   أخرىwas then recooled to −70° C.
6. 6
   workup.STIRRINGto stir
7. 7
   درجة الحرارةwarm to room temperature overnight
8. 8
   درجة الحرارةThe solution was cooled to −70° C.
9. 9
   workup.STIRRINGThe resulting slurry was stirred for one hour at −70° C.
10. 10
    درجة الحرارةwarmed to −10° C. over a two-hour period
11. 11
    أخرىrecooled to −70° C
12. 12
    درجة الحرارةto warm to room temperature overnight
13. 13
    أخرىThe mixture was quenched with water
14. 14
    أخرىthe layers were separated
15. 15
    غسيلThe organic layer was washed twice with sodium bicarbonate solution and with salt brine
16. 16
    تجفيفthen dried over magnesium sulfate
17. 17
    أخرىThe solvents were evaporated under vacuum
18. 18
    workup.DISTILLATIONthe product distilled twice under vacuum

الإجراء التجريبي

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.

المصدر