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Potassium Carbonate → 1,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 2206927
Notes
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Reaction equation

HRID 2206927 reaction equation
BrC1C=C(Cl)C=C(Cl)C=1F.FC(F)(F)C(B(O)O)=C.C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:32]=[C:31]([C:33]([C:35]([F:38])([F:37])[F:36])=[CH2:34])[C:30]([F:39])=[C:29]([Cl:40])[C:28]=1F>O1CCCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[Cl:40][C:29]1[CH:28]=[C:27]([Cl:26])[CH:32]=[C:31]([C:33]([C:35]([F:36])([F:37])[F:38])=[CH2:34])[C:30]=1[F:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 2782677(3,3,3-Trifluoroprop-1-en-2-yl)boronic acidHCID 509978971-Bromo-3,5-dichloro-2-fluorobenzeneHCID 866850801,3-Dichloro-2,4-difluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 871590141,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

1-bromo-3,5-dichloro-2-fluorobenzene (10 g), (3,3,3-trifluoroprop-1-en-2-yl)-boronic acid (7.5 g) and potassium carbonate (13.6 g) were dissolved in tetrahydrofuran (41 ml) and water (20 ml), and then deaerated. Dichlorobis(triphenylphosphine)palladium (II) (1.4 g) was added thereto and the mixture was stirred for 3 hours under reflux under argon atomosphere. After cooling the mixture to the room temperature, water and n-hexane were added, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was distilled off under reduced pressure, and the residue was roughly purified by silica gel chromatography (n-hexane) to obtain a mixture containing 1,3-dichloro-2,4-difluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene and hexane.

Workup

  1. temperatureunder reflux under argon atomosphere
  2. additionwere added
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was roughly purified by silica gel chromatography (n-hexane)
  8. customto obtain a mixture

Sources & evidence

ORD record
ord-371fd72d8e624aa7a9fb9e25e228fb37
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09375000B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes