반응 #2507816

반응 방정식

dimethyladamantyl bromide

1,1,1,4,4-pentachloro-1,4-disilabutane

allylbromide

3,5-dimethyladamantylbromide

→

1,1,1,4,4-Pentachloro-7-(3,5-dimethyladamantyl)-1,4-disilaheptane

용매

pentane

반응 조건

후처리

1. 1
   온도The solution was cooled to below −10° C. by ice/acetone bath
2. 2
   기타10° C.
3. 3
   workup.STIRRINGsolution was stirred for an additional two hours after which GC-MS
4. 4
   기타had reacted
5. 5
   세척it was washed twice with 500 ml water
6. 6
   기타The organic layer was collected
7. 7
   기타pentane was evaporated
8. 8
   workup.DISSOLUTIONRemaining material was dissolved to 700 ml ethanol
9. 9
   workup.ADDITIONa small amount of water was added
10. 10
    온도The solution was then heated up
11. 11
    온도to reflux
12. 12
    workup.STIRRINGit was stirred for 15 h
13. 13
    온도After cooling down to room temperature the solution
14. 14
    여과was filtered
15. 15
    workup.ADDITION300 ml water was added
16. 16
    추출the product was extracted
17. 17
    세척by washing twice with 500 ml pentane
18. 18
    기타Pentane layers were collected
19. 19
    세척washed once with water
20. 20
    기타The organic layer were collected
21. 21
    건조dried with anhydrous magnesium sulfate
22. 22
    여과filtered
23. 23
    기타Pentane was evaporated
24. 24
    workup.DISTILLATIONwas purified by distillation, yield 45.90 g (67%)
25. 25
    기타1-allyl-3,5-dimethyladamantane was moved to a 100 ml vessel
26. 26
    온도The solution was heated up to 85° C.
27. 27
    workup.ADDITIONAfter addition
28. 28
    온도the solution was heated up to 100° C.
29. 29
    workup.STIRRINGit was stirred for an hour
30. 30
    기타The product thus obtained
31. 31
    workup.DISTILLATIONwas then purified by distillation
32. 32
    기타yielding 53.54 g (51%), bp. 157-158° C./<0.5 mbar

실험 절차

81.71 g (0.336 mol) 3,5-dimethyladamantylbromide was dissolved in 500 ml pentane. The solution was cooled to below −10° C. by ice/acetone bath. 51.40 g (0.425 mol) allylbromide was added followed by 410 mg FeBr3. The solution was then stirred for three hours at −20 . . . 10° C. after which analysis by GC-MS was carried out, indicating that some unreacted starting materials remained. 420 mg FeBr3 was added and solution was stirred for an additional two hours after which GC-MS showed that all the dimethyladamantyl bromide had reacted. The solution was warmed up to room temperature and it was washed twice with 500 ml water. The organic layer was collected and pentane was evaporated. Remaining material was dissolved to 700 ml ethanol and a small amount of water was added followed by 25 g (0.382 mol) metallic zinc. The solution was then heated up to reflux and it was stirred for 15 h. After cooling down to room temperature the solution was filtered. 300 ml water was added and the product was extracted by washing twice with 500 ml pentane. Pentane layers were collected and washed once with water. The organic layer were collected, dried with anhydrous magnesium sulfate and filtered. Pentane was evaporated and remaining crude 1-allyl-3,5-dimethyladamantane was purified by distillation, yield 45.90 g (67%). 1-allyl-3,5-dimethyladamantane was moved to a 100 ml vessel followed by 50 μl H2PtCl6/IPA solution. The solution was heated up to 85° C. and 59.50 g (0.227 mol) 1,1,1,4,4-pentachloro-1,4-disilabutane was added slowly during 30 min. After addition, the solution was heated up to 100° C. and it was stirred for an hour. The product thus obtained was then purified by distillation yielding 53.54 g (51%), bp. 157-158° C./<0.5 mbar.

출처