Acetonitrile → HCID 117899759, compound

HRID 522442Notes

Reaction equation

HRID 522442 reaction equation
C(#N)C.[Cl:4][C:5]1[C:10]([S:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]([OH:17])=[C:7]([F:18])[CH:6]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OC(=O)C)C.CCCCCC>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:17][C:8]1[CH:9]=[C:10]([S:11][CH2:12][C:13]([F:14])([F:15])[F:16])[C:5]([Cl:4])=[CH:6][C:7]=1[F:18]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 117899711HCID 117899711, compound

Product 1

HCID 117899759HCID 117899759, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To 60 ml of acetonitrile were added 3.0 g (11.5 mmol) of 4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenol, 13.2 g (57.4 mmol) of 1,5-dibromopentane, 2.1 g (15.0 mmol) of potassium carbonate and 0.37 g (1.15 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 1.5 hour under heating. The mixture was allowed to cool to room temperature, and insoluble matters were removed by filtration. Then the filtrate was concentrated 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 4.2 g (yield: 89%) of an intended product.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hour
  2. temperatureunder heating
  3. custominsoluble matters were removed by filtration
  4. concentrationThen the filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-cc84f46bf7f14dcb9b50afc2f539d3a3
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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