Sodium Iodide → Dimesityl disulfide

HRID 2184163Notes

Reaction equation

HRID 2184163 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=O)=O.[Na+].[I-].FCC(O[C:21](=O)[CH2:22]F)=O>CC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10][S:10][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 130462-Mesitylenesulfonyl chlorideHCID 67886Acetic acid, 2-fluoro-, 1,1'-anhydride

Product 1

HCID 345613Dimesityl disulfide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,4,6-trimethylphenylsulfonyl chloride (500 mg, 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 2,4,6-trimethylphenyldisulfide as a light yellow crystalline compound (231 mg, 0.76 mmol, 67% 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-66600d1abbe64ed2958ff894b380c2be
Source dataset
uspto-grants-2005_05
Patent number
US06900307B1

Reaction notes

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