Potassium Iodide → 3-(4-(Trifluoromethylthio)-phenoxy)-3-methyl-1-butyne

HRID 2371935Notes

Reaction equation

HRID 2371935 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:9][C:10]([F:20])([F:19])[S:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.Cl[C:22]([CH3:26])([CH3:25])[C:23]#[CH:24]>CC(=O)CC>[F:20][C:10]([F:19])([F:9])[S:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:22]([CH3:26])([CH3:25])[C:23]#[CH:24])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 706791-Butyne, 3-chloro-3-methyl-2×HCID 38151584-(Trifluoromethylsulfanyl)phenol

Product 1

HCID 148574293-(4-(Trifluoromethylthio)-phenoxy)-3-methyl-1-butyne

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

13.8 g (0.1 mol) of dried potassium carbonate and 1.6 g (0.01 mol) of potassium iodide are suspended in a solution of 19.4 g (0.1 mol) of 4-(trifluoromethylthio)phenol in 250 ml of dry butanone and 15.4 g (0.15 mol) of 3-chloro-3-methyl-1-butyne are added dropwise. The mixture is then heated under reflux with stirring for 20 hours, 15.4 g of 3-chloro-3-methyl-1-butyne and 13.8 g of potassium carbonate are added once again and the mixture is further heated under reflux for 40 hours. Inorganic constituents are filtered off, the solution is concentrated, and the residue is taken up in 200 ml of methylene chloride and extracted using 1N NaOH solution. The organic phase is washed with water, dried and concentrated, and the residue is filtered through silica gel.

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux
  4. temperaturethe mixture is further heated
  5. temperatureunder reflux for 40 hours
  6. filtrationInorganic constituents are filtered off
  7. concentrationthe solution is concentrated
  8. extractionextracted
  9. washThe organic phase is washed with water
  10. customdried
  11. concentrationconcentrated
  12. filtrationthe residue is filtered through silica gel

Sources & evidence

ORD record
ord-136e2603f0e241fab0ea03cc6469d5dc
Source dataset
uspto-grants-1992_03
Patent number
US05096914

Reaction notes

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