Cyclopentanone → 2-(2-Bromo-4-fluorophenyl)cyclopentanone

HRID 558124Notes

Reaction equation

HRID 558124 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1I.[C:10]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:12][CH2:13][CH2:14][C:10]1=[O:15]

Participants

7

Reactant 3

HCID 8452CyclopentanoneHCID 10796Cesium carbonateHCID 27733722-Bromo-4-fluoro-1-iodobenzene

Product 1

HCID 574450742-(2-Bromo-4-fluorophenyl)cyclopentanoneYield 15%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 2-bromo-4-fluoro-1-iodobenzene (4.5 g, 15 mmol), cyclopentanone (2.65 mL, 29.9 mmol), cesium carbonate (10.72 g, 32.9 mmol), 4,5-bis(disphenylphosphino)-9,9-dimethylxanthene (0.54 g, 0.9 mmol), and Palladium2(dibenzalacetone)3 [Pd2(dba)3)](0.35 g, 0.37 mmol) in dioxane (10 mL) to 80° C. under N2 for 22 h. After cooling the mixture to RT, dilute with ether, filter through a celite pad, and remove the solvent. Purify the residue by column chromatography (hexane:ether/20:1) to give the title compound (0.55 g, 15%). MS (GC) m/z 258 [M]+.

Workup

  1. temperatureHeat
  2. filtrationfilter through a celite pad
  3. customremove the solvent
  4. customPurify the residue by column chromatography (hexane:ether/20:1)

Sources & evidence

ORD record
ord-8dd603b7aa014c309d887096abaebb0c
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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