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

HRID 1500192Notes

Reaction equation

HRID 1500192 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]

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 86685080HCID 86685080, compound

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 atmosphere. 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 atmosphere
  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-a5b41f17d3104a4db202952497247db4
Source dataset
uspto-grants-2015_12
Patent number
US09206122B2

Reaction notes

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