Hydrogen Bromide → Triphenylsulfonium Bromide

HRID 2915

反応式

HRID 2915 の反応式
[C:1]1([Mg][Br:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:10]1([S:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br>C1C=CC=CC=1.CCOCC.ClCCl>[Br-:8].[C:1]1([S+:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 260Hydrogen BromideHCID 962WaterHCID 13679Diphenyl sulfoxideHCID 178418255HCID 178418255、化合物

生成物 1

HCID 11984010Triphenylsulfonium Bromide

試薬・触媒・溶媒 3

HCID 241Benzene溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

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%).

後処理

  1. customTo a 3-necked 1 L round bottom flask equipped with a still head
  2. customthe diethyl ether removed under vacuo
  3. temperatureby gently heating
  4. additionAdditional benzene (150 ml) was added
  5. temperaturea gentle reflux under nitrogen
  6. additionOnce the addition
  7. temperaturethe reaction mixture was heated at
  8. temperaturea gentle reflux for 3 hours
  9. temperatureThe reaction mixture was cooled (ice bath temperature)
  10. customAfter separation of the layers
  11. extractionthe organic layer extracted
  12. extractionextracted with dichloromethane (200 ml)
  13. dry with materialdried (MgSO4 )
  14. concentrationconcentrated in vacuo
  15. customto give the crude product as an off-white solid (14.50 g)
  16. additionadded
  17. customto precipitate the salt
  18. temperatureThe suspension was cooled in an ice bath for 1 hour
  19. customto collecting the salt
  20. washwashing with ether

出典と根拠

ORDレコード
ord-3d99672bc286434e8155aafff5a7504c
出典データセット
uspto-grants-1998_03
特許番号
US05731364

関連ノート

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