Chlorotrimethylsilane → Tris(4-tert-butoxyphenyl)sulfonium chloride

HRID 399959Notes

Reaction equation

HRID 399959 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[Si]([Cl:36])(C)C.[C:37]([O:41][C:42]1[CH:47]=[CH:46][C:45](Cl)=[CH:44][CH:43]=1)([CH3:40])([CH3:39])[CH3:38].[Mg].[Cl-].[NH4+]>C1COCC1.C(Cl)(Cl)Cl>[Cl-:36].[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S+:12]([C:45]2[CH:46]=[CH:47][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:43][CH:44]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 1404581-Chloro-4-tert-butoxybenzeneHCID 5462224MagnesiumHCID 15389810Bis(4-tert-butoxyphenyl) sulfoxide

Product 1

HCID 85759090Tris(4-tert-butoxyphenyl)sulfonium chlorideYield 35%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17.8 g (0.052 mol) of bis(4-tertbutoxyphenyl) sulfoxide in 52 g of THF was cooled on an ice bath. To the solution, 5.3 g (0.052 mol) of triethylamine was added and 14.1 g (0.13 mol) of trimethylsilyl chloride was dropwised at 0° to 10° C. Stirring was continued at 0 to 10° C. for 30 minutes. To this solution, a Grignard reagent which was conventionally prepared from 24.0 g (0.13 mol) of 4-tert-butoxychlorobenzene, 3.2 g (0.13 mol) of magnesium, and 40 g of THF was dropwised at 0° to 10° C. Stirring was continued at 0° to 10° C. for 30 minutes. 300 g of 20% ammonium chloride aqueous solution was added to the reaction mixture. To the organic layer was added 500 g of chloroform. The organic layer was washed twice with 200 g of water and the solvent was evaporated and residue was purifie by column chromatography (silica gel, eluent: chloroform/methanol), isolating 9.3 g (yield 35%) of tris(4-tert-butoxyphenyl)sulfonium chloride with 99% purity.

Workup

  1. customwas dropwised at 0° to 10° 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 washed twice with 200 g of water
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e721bbc8b2e044319a53e787de2ae595
Source dataset
uspto-grants-1998_10
Patent number
US05824824

Reaction notes

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