반응 #3011

반응 방정식

hydrobromic acid

water

phenylmagnesium bromide

phenyl sulfoxide

→

triphenylsulfonium bromide

용매

benzene

ether

dichloromethane

benzene

반응 조건

후처리

1. 1
   기타To a 3-necked 1 L round bottom flask equipped with a still head
2. 2
   기타the diethyl ether removed under vacuo
3. 3
   온도by gently heating
4. 4
   workup.ADDITIONAdditional benzene (150 ml) was added
5. 5
   온도a gentle reflux under nitrogen
6. 6
   workup.ADDITIONOnce the addition
7. 7
   온도the reaction mixture was heated at
8. 8
   온도a gentle reflux for 3 hours
9. 9
   온도The reaction mixture was cooled (ice bath temperature)
10. 10
    기타After separation of the layers
11. 11
    추출the organic layer extracted
12. 12
    추출extracted with dichloromethane (200 ml)
13. 13
    건조dried (MgSO4 )
14. 14
    농축concentrated in vacuo
15. 15
    기타to give the crude product as an off-white solid (14.50 g)
16. 16
    workup.ADDITIONadded
17. 17
    기타to precipitate the salt
18. 18
    온도The suspension was cooled in an ice bath for 1 hour
19. 19
    기타to collecting the salt
20. 20
    세척washing with ether

실험 절차

To a 3-necked 1 L round bottom flask equipped with a still head was added phenylmagnesium bromide (3 M in diethyl ether, 142 ml, 0.426 mol) followed by dry benzene (150 ml). The flask was connected to a water aspirator and the diethyl ether removed under vacuo by gently heating. Additional benzene (150 ml) was added and the solution brought to a gentle reflux under nitrogen. A solution of phenyl sulfoxide (17.23 g, 85.2 mmol) in benzene (100 ml) was added dropwise over 1.5 hours. Once the addition was complete, the reaction mixture was heated at a gentle reflux for 3 hours. The reaction mixture was cooled (ice bath temperature) while adding a solution of hydrobromic acid (25%, 200 ml). The resulting biphasic mixture was stirred at room temperature overnight. After separation of the layers, the organic layer extracted were combined and extracted with dichloromethane (200 ml), dried (MgSO4 ) and concentrated in vacuo to give the crude product as an off-white solid (14.50 g). The solid was taken up in the minimum mount of warm dichloromethane (100 ml) and four times the volume of ether added to precipitate the salt. The suspension was cooled in an ice bath for 1 hour prior to collecting the salt and washing with ether. In this way, triphenylsulfonium bromide was isolated as a white solid (14.40 g, 49%).

출처