Acetonitrile → 6-Bromohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl]ether
Reaction equation
C(#N)C.[Cl:4][C:5]1[CH:10]=[C:9]([Cl: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(OC(=O)C)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:15])([F:17])[F:16])[C:9]([Cl:11])=[CH:10][C:5]=1[Cl:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 30 ml of acetonitrile were added 1.0 g (3.61 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenol, 3.5 g (14.4 mmol) of 1,6-dibromohexane, 0.65 g (15.0 mmol) of potassium carbonate and 0.12 g (0.37 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 3 hours under heating. The mixture was allowed to stand at 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 1.51 g (yield: 95%) of an intended product.
Workup
- temperatureThe mixture was refluxed for 3 hours
- temperatureunder heating
- customto stand at room temperature
- custominsoluble matters were removed by filtration
- concentrationThen the filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (
Sources & evidence
- ORD record
- ord-4209d747b1f74598a4cb40d72daf6bcb
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09332754B2
Reaction notes
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