Cesium fluoride → 2-(2',4'-Dichloro-4-cyclopropylbiphenyl-3-yl)-cyclopentane-1,3-dione

HRID 40480Notes

Reaction equation

HRID 40480 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:15]2[CH2:17][CH2:16]2)=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1B(O)O.[F-].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:2]1[CH:3]=[CH:4][C:5]([CH:15]2[CH2:17][CH2:16]2)=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 666768602-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

Product 1

HCID 669914682-(2',4'-Dichloro-4-cyclopropylbiphenyl-3-yl)-cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione (0.100 g, 0.34 mmol), 2,4-dichlorophenylboronic acid (0.090 g, 0.47 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]palladium(II)chloride (22 mg, 0.027 mmol) and cesium fluoride (0.152 g, 1.0 mmol) is added 1,2-dimethoxyethane (1 ml). After evacuating and flushing with nitrogen (×3) the mixture is heated at 160° C. for 15 minutes under microwave irradiation. After dilution with distilled water the crude product is extracted with ethyl acetate (×3), and the organic phase is washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is then purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant) and further triturated with hexanes to afford 2-(2′,4′-dichloro-4-cyclopropylbiphenyl-3-yl)-cyclopentane-1,3-dione as a white powder.

Workup

  1. customAfter evacuating
  2. customflushing with nitrogen (×3) the mixture
  3. extractionAfter dilution with distilled water the crude product is extracted with ethyl acetate (×3)
  4. washthe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product is then purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant)
  8. customfurther triturated with hexanes

Sources & evidence

ORD record
ord-f9debeb7e7ec4267bfd5613e8c24221f
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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