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

HRID 443197노트

반응식

HRID 443197 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d83c15934ea4740b197b30007d7d5c1
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05892131

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