Chlorotrimethylsilane → (4-tert-Butoxyphenyl)(diphenyl)sulfanium chloride

HRID 399961Notes

Reaction equation

HRID 399961 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(N(CC)CC)C.C[Si]([Cl:26])(C)C.[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35](Cl)=[CH:34][CH:33]=1)([CH3:30])([CH3:29])[CH3:28].[Mg].[Cl-].[NH4+]>C(Cl)Cl.C(Cl)(Cl)Cl.C1COCC1>[Cl-:26].[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35]([S+:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:34][CH:33]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

10

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13679Diphenyl sulfoxideHCID 25517Ammonium ChlorideHCID 1404581-Chloro-4-tert-butoxybenzeneHCID 5462224Magnesium

Product 1

HCID 23435201(4-tert-Butoxyphenyl)(diphenyl)sulfanium chlorideYield 72%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.2 g (0.10 mol) of diphenyl sulfoxide in 200 g of methylene chloride was cooled on an ice bath. To the solution, 5.3 g (0.052 mol) of triethylamine was added and 32.6 g (0.30 mol) of trimethylsilyl chloride was dropwised at 0° to 20° C. Stirring was continued at 0° to 10° C. for 15 minutes. To this solution, a Grignard reagent which was conventionally prepared from 55.4 g (0.30 mol) of 4-tert-butoxychlorobenzene, 7.3 g (0.30 mol) of magnesium, and 90 g of THF was dropwised at 0° to 10 ° C. Stirring was continued at 0° to 10° C. for 30 minutes. 500 g of 20% ammonium chloride aqueous solution was added to the reaction mixture. To the organic layer was added 1,000 g of chloroform. The organic layer was once washed with 200 g of water and the solvent was evaporated. The residue was purified by recrystalization, isolating 26.6 g (yield 72%) of (4-tert-butoxyphenyl)diphenylsulfonium chloride with 98% purity.

Workup

  1. customwas dropwised at 0° to 20° C
  2. customwas dropwised at 0° to 10 ° C
  3. stirringStirring
  4. waitwas continued at 0° to 10° C. for 30 minutes
  5. washThe organic layer was once washed with 200 g of water
  6. customthe solvent was evaporated
  7. customThe residue was purified by recrystalization

Sources & evidence

ORD record
ord-cb7a8603eac2402fb2ec6149732e1e32
Source dataset
uspto-grants-1998_10
Patent number
US05824824

Reaction notes

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