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

HRID 1458390
ノート
印刷プレビュー

反応式

HRID 1458390 の反応式
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>[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1-bromo-4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentene, (Z)- (1.02 g, 3.5 mmol), and bis(di-benzylideneacetone)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.

後処理

  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

出典と根拠

ORDレコード
ord-deeaaa57cec5403a808655c6a2742276
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849958

反応ノート

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