Hydrochloric Acid → Triphenylsulfonium chloride

HRID 553383Notes

Reaction equation

HRID 553383 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>ClCCl.C(OCC)C.O.O1CCCC1>[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

Diphenyl sulfoxide, 40 g (0.2 mole), was dissolved in 400 g of dichloromethane, which was stirred under ice cooling. At a temperature below 20° C., 65 g (0.6 mole) of trimethylsilyl chloride was added dropwise to the solution, which was aged for 30 minutes at the temperature. Then, a Grignard reagent which had been prepared from 14.6 g (0.6 mole) of metallic magnesium, 67.5 g (0.6 mole) of chlorobenzene and 168 g of tetrahydrofuran (THF) was added dropwise at a temperature below 20° C. The reaction solution was aged for one hour, after which 50 g of water at a temperature below 20° C. was added to quench the reaction. To this solution, 150 g of water, 10 g of 12N hydrochloric acid, and 200 g of diethyl ether were further added. The water layer was separated and washed with 100 g of diethyl ether, yielding an aqueous solution of triphenylsulfonium chloride. The compound in aqueous solution form was used in the subsequent reaction without further isolation.

Workup

  1. additionwas added dropwise at a temperature below 20° C
  2. waitThe reaction solution was aged for one hour
  3. customto quench
  4. customthe reaction
  5. customThe water layer was separated
  6. washwashed with 100 g of diethyl ether

Sources & evidence

ORD record
ord-991224432001483c93a0aff8422aef27
Source dataset
uspto-grants-2011_11
Patent number
US08048610B2

Reaction notes

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