Hydrochloric Acid → Bis(3,5-dimethylphenyl)-(4-fluorophenyl)-sulfonium bromide

HRID 1753689Notes

Reaction equation

HRID 1753689 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:11]=[C:12]([S:17]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=2)=O)[CH:13]=[C:14]([CH3:16])[CH:15]=1.C[Si](Cl)(C)C.Cl>C(Cl)Cl>[Br-:1].[CH3:26][C:21]1[CH:20]=[C:19]([S+:17]([C:12]2[CH:11]=[C:10]([CH3:9])[CH:15]=[C:14]([CH3:16])[CH:13]=2)[C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)[CH:24]=[C:23]([CH3:25])[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 99931-Bromo-4-fluorobenzeneHCID 23396604Bis(3,5-dimethylphenyl) sulfoxide

Product 1

HCID 131733660Bis(3,5-dimethylphenyl)-(4-fluorophenyl)-sulfonium bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a Grignard reagent prepared from 79 g of 1-bromo-4-fluorobenzene, 13 g of bis(3,5-dimethylphenyl) sulfoxide obtained in Synthesis Example 1-46 and 50 g of methylene chloride were added. Under ice cooling, 16 g of trimethylsilyl chloride was added dropwise to the solution, which was aged for 30 minutes. To the reaction solution, 50 g of 3 wt % dilute hydrochloric acid was added to quench the reaction. The organic layer was separated. Without further purification, it was ready for use in the subsequent reaction.

Workup

  1. additionwere added
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. customWithout further purification, it
  6. customwas ready for use in the subsequent reaction

Sources & evidence

ORD record
ord-b75875943a4d4c4c82389f1e964d4cff
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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