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

HRID 1806138Notes

Reaction equation

HRID 1806138 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-098818b602634afb8eb491acc96a9814
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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