Sodium Thiosulfate → 2,4-Dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenol
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[OH:15].ClC1C=CC=C(C(OO)=[O:24])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9]([CH2:10][C:11]([F:12])([F:14])[F:13])=[O:24])=[CH:4][C:3]=1[OH:15]Participants
Procedure
In 80 ml of chloroform was dissolved 10.0 g (36.08 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenol. Thereto was added 9.80 g (39.75 mmol) of 3-chloroperbenzoic acid (purity: about 70%) under ice cooling, and the mixture was stirred for 30 minutes at room temperature. Then, saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to decompose excess peroxide. Thereafter, the solvent was distilled off under reduced pressure, and extraction was conducted by adding ethyl acetate and water. The organic phase obtained was washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to obtain 9.30 g (yield: 88%) of an intended product.
Workup
- distillationThereafter, the solvent was distilled off under reduced pressure, and extraction
- additionby adding ethyl acetate and water
- customThe organic phase obtained
- washwas washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-a89b3c196e1d44bc8937ee2a5455e52a
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09332754B2
Reaction notes
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