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Potassium Carbonate → 4-(p-Chlorophenyl)-3-fluoro-1-(4-fluoro-3-phenoxyphenyl)-4-methyl-2-pentene

HRID 1977711
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HRID 1977711 반응식
Br[CH2:2][CH:3]=[C:4]([F:15])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][C:24]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(Cl)Cl.CCCCCC>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([CH3:7])([CH3:6])[C:4]([F:15])=[CH:3][CH2:2][C:26]2[CH:27]=[CH:28][C:23]([F:22])=[C:24]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:25]=2)=[CH:9][CH:10]=1
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참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 21185404(4-Fluoro-3-phenoxyphenyl)-boronic acidHCID 21226440Methylenechloride HexaneHCID 542729131-Bromo-4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentene

생성물 1

HCID 545425684-(p-Chlorophenyl)-3-fluoro-1-(4-fluoro-3-phenoxyphenyl)-4-methyl-2-pentene수율 85.6%

시약·촉매·용매 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매
HCID 702Ethanol용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-bromo-4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentene, (Z)- (1.02 g, 3.5 mmol), and bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] (0.1 g, 0.17 mmol) in toluene (20 mL) under nitrogen is stirred for one minute, treated with potassium carbonate (1.94 g, 0.014 mol), degassed, treated with a solution of 4-fluoro-3-phenoxybenzeneboronic acid (1.05 g, 4.55 mmol) in ethanol (5 mL), refluxed for 50 minutes, cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate is washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a 15:100 methylene chloride/hexane solution gives the title compound as a colorless oil (1.19 g, 85.6% yield) which is identified by NMR spectral analyses.

후처리

  1. customdegassed
  2. temperaturerefluxed for 50 minutes
  3. filtrationfiltered through diatomaceous earth
  4. washThe filtrate is washed sequentially with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

출처 및 근거

ORD 기록
ord-2afcb871416f452299004c3ae569f863
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06235754B1

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