Acetonitrile → HCID 117899784, compound

HRID 522455Notes

Reaction equation

HRID 522455 reaction equation
C(#N)C.[CH3:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:7][C:6]=1[OH:18].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:18][C:6]1[CH:7]=[C:8]([S:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:9]([CH3:11])=[CH:10][C:5]=1[CH3:4]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 117899776HCID 117899776, compound

Product 1

HCID 117899784HCID 117899784, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 60 ml of acetonitrile were added 1.14 g (4.83 mmol) of 2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenol, 4.71 g (19.31 mmol) of 1,6-dibromohexane, 0.73 g (5.28 mmol) of potassium carbonate and catalytic amount of tetra-n-butylammonium bromide. The mixture was refluxed for 3 hours under heating. The mixture was allowed to cool to room temperature, and insoluble matters were removed by filtration. Then the solvent of filtrate 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=40:1˜20:1), to obtain 1.87 g (yield: 97%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperatureunder heating
  3. custominsoluble matters were removed by filtration
  4. distillationThen the solvent of filtrate was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-16eb39d116c3448e8632179d372b2782
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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