Hydrogen Bromide → Triphenylsulfonium Bromide

HRID 1111477Notes

Reaction equation

HRID 1111477 reaction equation
[C:1]1([Mg][Br:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)C.[C:14]1([S:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Br>C1C=CC=CC=1.CCCCCCC.C1(C)C=CC=CC=1>[Br-:8].[C:1]1([S+:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 13679Diphenyl sulfoxideHCID 178418255HCID 178418255, compound

Product 1

HCID 11984010Triphenylsulfonium BromideYield 44%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

A 3.0 M solution of phenylmagnesium bromide in diethyl ether (42 ml, 0.126 mole) was distilled under vacuum with slow heating from 20° to 80° C. Toluene (40 ml) was added, followed by n-heptane (200 ml). The resulting mixture was stirred and a solution of diphenylsulfoxide 10.1 g, (0.050 mol), in benzene (60 ml) was added during 1 hour at 80° C. The mixture was stirred for 3 hours and cooled to room temperature. An 25% aqueous hydrobromic acid solution (180 ml) was slowly added to the reaction mixture (exotherm-). The layers were separated and the organic layer was extracted twice with 5% aqueous hydrobromic acid (2×30 ml). The combined aqueous extracts were extracted three times with dichloromethane (3×250 ml). The dichloromethane extracts were dried over magnesium sulfate, filtered and the organic solvent evaporated to leave a residue which was crystallized from dichloromethane/diethyl ether to give triphenylsulfonium bromide (7.7 g, 44%).

Workup

  1. temperaturewith slow heating from 20° to 80° C
  2. stirringThe mixture was stirred for 3 hours
  3. customThe layers were separated
  4. extractionthe organic layer was extracted twice with 5% aqueous hydrobromic acid (2×30 ml)
  5. extractionThe combined aqueous extracts were extracted three times with dichloromethane (3×250 ml)
  6. dry with materialThe dichloromethane extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe organic solvent evaporated
  9. customto leave a residue which
  10. customwas crystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-50fecda25d874d3585b912e5b2d3766b
Source dataset
uspto-grants-1990_12
Patent number
US04980492

Reaction notes

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