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Potassium Carbonate → 1-(4-Chlorophenyl)-1-(2-fluoro-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl)cyclopropane

HRID 1385644
ノート
印刷プレビュー

反応式

HRID 1385644 の反応式
[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(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[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[CH:21]=[CH:22][C:17]([F:16])=[C:18]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 211854051-(4-Chlorophenyl)-1-(2-fluoro-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl)cyclopropane収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 1140
Toluene
溶媒

実験手順

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-phenoxybenzene-boronic acid (0.452 g, 1.95 mmol), potassium carbonate (1.86 g, 13.5 mmol) and bis(dibenzylideneacetone)-palladium(O) (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.

後処理

  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

出典と根拠

ORDレコード
ord-dd21a8bbea0a45a8a1008262cd4bbe26
出典データセット
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06262319B1

反応ノート

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