Sodium Iodide → 3,4-Dimethoxyphenyldisulfide

HRID 2184162

Reaction equation

HRID 2184162 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11](Cl)(=O)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Na+].[I-].FC[C:19]([O:21][C:22](=O)[CH2:23]F)=O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][S:11][C:5]2[CH:6]=[CH:23][C:22]([O:21][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 67886Acetic acid, 2-fluoro-, 1,1'-anhydrideHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 112677463,4-Dimethoxyphenyldisulfide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,4-dimethoxyphenylsulfonyl chloride (2.3 mmol) was dissolved in acetone (60 mL), and then NaI (3.4 g, 23 mmol) and fluoroacetic anhydride (1.45 mL, 6.9 mmol) were added and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated, water was added, extraction was performed with ether and the organic layer was further washed with aqueous sodium thiosulfate, water and saturated saline. After drying over magnesium sulfate and vacuum concentration, the residue was purified with a silica gel column (hexane) to obtain 3,4-dimethoxyphenyldisulfide as a light yellow crystalline compound (58% yield). The NMR and mass spectral data for the obtained compound were as follows:

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwater was added
  3. extractionextraction
  4. washthe organic layer was further washed with aqueous sodium thiosulfate, water and saturated saline
  5. dry with materialAfter drying over magnesium sulfate and vacuum concentration
  6. customthe residue was purified with a silica gel column (hexane)

Sources & evidence

ORD record
ord-03b07f8954b243fda6cc6cb8b2bc2cb9
Source dataset
uspto-grants-2005_05
Patent number
US06900307B1

Linked notes

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