Hydrochloric Acid → Triphenylsulfonium chloride

HRID 219506

Reaction equation

HRID 219506 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.C[Si]([Cl:19])(C)C.[Mg].Cl[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>C(OCC)C.O.O1CCCC1.ClCCl>[Cl-:19].[C:1]1([S+:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7964ChlorobenzeneHCID 13679Diphenyl sulfoxideHCID 5462224Magnesium

Product 1

HCID 61343Triphenylsulfonium chloride

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into 400 g of dichloromethane was dissolved 40 g (0.2 mole) of diphenyl sulfoxide, and the resulting solution was agitated under ice-cool. And then, 65 g (0.6 mole) of trimethyl silyl chloride was added dropwise at the temperature not exceeding 20° C., at which temperature the mixture was aged for 30 minutes. Thereafter, a Grignard agent prepared separately from 14.6 g (0.6 mole) of a metal magnesium, 67.5 g (0.6 mol) of chlorobenzene, and 168 g of tetrahydrofurane (THF) was added dropwise into it at the temperature not exceeding 20° C. After the reaction mixture was aged for one hour, it was added by 50 g of water at the temperature not exceeding 20° C. to terminate the reaction, and then further by 150 g of water, 10 g of 12-N hydrochloric acid, and 200 g of diethyl ether. A water layer was taken out by separation and washed by 100 g of diethyl ether to obtain an aqueous triphenyl sulfonium chloride solution. This was used in the subsequent reaction without isolation procedures further.

Workup

  1. temperaturecool
  2. customexceeding 20° C., at which temperature
  3. additionwas added dropwise into it at the temperature not
  4. customexceeding 20° C
  5. waitAfter the reaction mixture was aged for one hour
  6. customexceeding 20° C.
  7. customto terminate
  8. customthe reaction
  9. customA water layer was taken out by separation
  10. washwashed by 100 g of diethyl ether

Sources & evidence

ORD record
ord-71d2164e01384454a1547b8371ff9982
Source dataset
uspto-grants-2012_06
Patent number
US08202677B2

Linked notes

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