Tetrahydrofuran → 6-Trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether

HRID 522448Notes

Reaction equation

HRID 522448 reaction equation
O1CCCC1.[S:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[C:20]([S:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:19]([Cl:28])=[CH:18][C:17]=1[Cl:29])C#N.[F:30][C:31]([Si](C)(C)C)([F:33])[F:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OC(=O)C)C.CCCCCC>[F:30][C:31]([F:33])([F:32])[S:6][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[C:20]([S:22][CH2:23][C:24]([F:27])([F:25])[F:26])[C:19]([Cl:28])=[CH:18][C:17]=1[Cl:29]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 1178996916-Thiocyanatohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether

Product 1

HCID 1178997306-Trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]etherYield 64%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To 30 ml of tetrahydrofuran were added 1.04 g (2.49 mmol) of 6-thiocyanatohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether and 1.06 g (7.45 mmol) of trifluoromethyltrimethylsilane. Thereto was added 0.25 ml (concentration: 1 mol/liter, 0.25 mmol) of tetrahydrofuran solution of tetra-n-butylammonium fluoride at 0° C., and reaction mixture was stirred for 2 hours at room temperature. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane ethyl acetate=20:1), to obtain 0.73 g (yield: 64%) of an intended product.

Workup

  1. customreaction mixture
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-6d6e905c972d4929a5c2d6759684e508
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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