Iodine → 1,2-Bis(2-(trifluoromethyl)phenyl)disulfane

HRID 911890Notes

Reaction equation

HRID 911890 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].II>C(#N)C>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:11])([F:10])[F:1]

Participants

4

Reactant 2

HCID 807IodineHCID 27778892-(Trifluoromethyl)benzenethiol

Product 1

HCID 113256811,2-Bis(2-(trifluoromethyl)phenyl)disulfaneYield 88.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(trifluoromethyl)benzenethiol (0.185 mL, 1.40 mmol) in wet acetonitrile (1:5 water/acetonitrile) was added Iodine (0.178 g, 0.702 mmol) and allowed to stir over night at room temperature. The reaction was concentrated, then diluted with EtOAc and quenched with aqueous sodium thiosulfate, extracted and dried organic with brine, Na2SO4, filtered and concentrated to afford the title compound (219 mg, 44% yield) as a colorless oil.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with EtOAc
  3. customquenched with aqueous sodium thiosulfate
  4. extractionextracted and dried organic with brine, Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-538faa91f2724abd801a42579087118f
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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