Hydrogen Bromide → Triphenylsulfonium Bromide

HRID 584040Notes

Reaction equation

HRID 584040 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si](C)(C)C.[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Mg].Br>O1CCCC1.C1(C)C=CC=CC=1>[Br-:20].[C:1]1([S+:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 6397ChlorotrimethylsilaneHCID 7961BromobenzeneHCID 13679Diphenyl sulfoxideHCID 5462224Magnesium

Product 1

HCID 11984010Triphenylsulfonium BromideYield 68%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 600 ml of tetrahydrofuran were dissolved, 21.1 g (0.1 mol) of diphenylsulfoxide under nitrogen atmosphere, then 27.2 g (0.25 mol) of chlorotrimetylsilane was poured into them. A Grignard reagent prepared from 39.3 g (0.25 mol) of bromobenzene and 6.1 g of magnesium metal in accordance with the conventional manner was added dropwise thereto under ice-cooling, followed by allowing to react at the same temperature for 3 hours. After completion of the reaction, 500 ml of 24% aqueous solution of hydrobromic acid was added dropwise to the reaction solution at 0 to 5° C., and then 600 ml of toluene was poured into them, followed by stirring and separation, the organic layer was extracted twice with 120 ml of 12% aqueous solution of hydrobromic acid, and the resulting aqueous layers were combined and extracted 3 times with 480 ml of methylene chloride. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 23.3 g (yield: 68%) of triphenylsulfonium bromide as a white crystal.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooling
  3. customto react at the same temperature for 3 hours
  4. additionwas added dropwise to the reaction solution at 0 to 5° C.
  5. customseparation
  6. extractionthe organic layer was extracted twice with 120 ml of 12% aqueous solution of hydrobromic acid
  7. extractionextracted 3 times with 480 ml of methylene chloride
  8. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db7f071cf86f447bb87a3aef690c020d
Source dataset
uspto-grants-2005_08
Patent number
US06924323B2

Reaction notes

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