m-Chloroperbenzoic acid → 6-Trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether

HRID 522449Notes

Reaction equation

HRID 522449 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([Cl:23])=[CH:13][C:12]=1[Cl:24].ClC1C=CC=C(C(OO)=[O:35])C=1.C(OC(=O)C)C.CCCCCC>C(Cl)(Cl)Cl>[F:26][C:2]([F:1])([F:25])[S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([S:17]([CH2:18][C:19]([F:20])([F:21])[F:22])=[O:35])[C:14]([Cl:23])=[CH:13][C:12]=1[Cl:24]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 1178997306-Trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether

Product 1

HCID 1178997506-Trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]etherYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 30 ml of chloroform was dissolved 0.53 g (1.15 mmol) of 6-trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether. Thereto was added 0.26 g (1.13 mmol) of 3-chloroperbenzoic acid (purity: about 75%) at 0° C., and the mixture was stirred for 3 hours at room temperature. Then, the solvent was distilled off under reduced pressure, 0.5 ml of triethylamine was added to the residue, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane ethyl acetate=5:1), to obtain 0.41 g (yield: 75%) of an intended product.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure, 0.5 ml of triethylamine
  2. additionwas added to the residue
  3. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-7ec1c4c8de6b4387b6d579f334f86280
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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