反応 #3011

反応方程式

hydrobromic acid

water

phenylmagnesium bromide

phenyl sulfoxide

→

triphenylsulfonium bromide

溶媒

benzene

ether

dichloromethane

benzene

反応条件

後処理

1. 1
   その他To a 3-necked 1 L round bottom flask equipped with a still head
2. 2
   その他the diethyl ether removed under vacuo
3. 3
   温度by gently heating
4. 4
   workup.ADDITIONAdditional benzene (150 ml) was added
5. 5
   温度a gentle reflux under nitrogen
6. 6
   workup.ADDITIONOnce the addition
7. 7
   温度the reaction mixture was heated at
8. 8
   温度a gentle reflux for 3 hours
9. 9
   温度The reaction mixture was cooled (ice bath temperature)
10. 10
    その他After separation of the layers
11. 11
    抽出the organic layer extracted
12. 12
    抽出extracted with dichloromethane (200 ml)
13. 13
    乾燥dried (MgSO4 )
14. 14
    濃縮concentrated in vacuo
15. 15
    その他to give the crude product as an off-white solid (14.50 g)
16. 16
    workup.ADDITIONadded
17. 17
    その他to precipitate the salt
18. 18
    温度The suspension was cooled in an ice bath for 1 hour
19. 19
    その他to collecting the salt
20. 20
    洗浄washing with ether

実験手順

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%).

出典