Potassium Carbonate → 1-(p-Chlorophenyl)-1-[2-fluoro-3-(4-fluoro-3-phenoxy-3-phenoxyphenyl)propenyl]cyclopropane

HRID 443197Notes

Reaction equation

HRID 443197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:11]=[C:12]([F:15])[CH2:13]Br)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:33](=[O:36])([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:11]=[C:12]([F:15])[CH2:13][C:20]3[CH2:19][C:18]([O:36][C:33]4[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=4)([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:17]([F:16])=[CH:22][CH:21]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 21185404(4-Fluoro-3-phenoxyphenyl)-boronic acidHCID 537657641-(p-Chlorophenyl)-1-(3-bromo-2-fluoropropenyl)cyclopropane

Product 1

HCID 867540491-(p-Chlorophenyl)-1-[2-fluoro-3-(4-fluoro-3-phenoxy-3-phenoxyphenyl)propenyl]cyclopropaneYield 63%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a mixture of 1-(p-chlorophenyl)-1-(3-bromo-2-fluoropropenyl)cyclopropane, (Z)- (0.434 g, 1.5 mmol), 4-fluoro-3-phenoxybenzeneboronic acid (0.452 g, 1.95 mmol), potassium carbonate (1.86 g, 13.5 mmol) and bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 4.3 mg, 0.075 mmol) in toluene is heated at 80° C. for one hour, cooled to room temperature, diluted with water, and filtered through diatomaceous earth. The phases are separated and the aqueous phase is extracted with ethyl acetate. The organic phase and ethyl acetate extract are combined, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 3:20 methylene chloride/hexanes solution gives the title product as an oil (0.274 g, 63% yield) which is identified by NMR spectral analyses.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. extractionThe organic phase and ethyl acetate extract
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-1d83c15934ea4740b197b30007d7d5c1
Source dataset
uspto-grants-1999_04
Patent number
US05892131

Reaction notes

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