Acetonitrile → HCID 117899761, compound

HRID 522439Notes

Reaction equation

HRID 522439 reaction equation
C(#N)C.[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[S:12][CH2:13][C:14]([F:17])([F:16])[F:15].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:24].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH3:4])=[C:6]([S:12][CH2:13][C:14]([F:15])([F:17])[F:16])[CH:7]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 117899720HCID 117899720, compound

Product 1

HCID 117899761HCID 117899761, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 100 ml of acetonitrile were added 2.5 g (11 mmol) of 4-methyl-3-(2,2,2-trifluoroethylthio)phenol, 2.5 g (13 mmol) of 1-bromo-5-chloropentane, 1.9 g (14 mmol) of potassium carbonate and 0.35 g (1.1 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 5 hours under heating and then allowed to cool to room temperature. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 2.9 g (yield: 79%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-80f5a2f55d7d49b6851967cd8a3a2076
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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