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

HRID 443199ノート

反応式

HRID 443199 の反応式
Br[CH2:2][C:3]([F:15])=[CH:4][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>C1(C)C=CC=CC=1.C(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])[CH:4]=[C:3]([F:15])[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

7

反応物 3

HCID 11430Potassium CarbonateHCID 21185404(4-Fluoro-3-phenoxyphenyl)-boronic acidHCID 537394791-Bromo-4-(p-chlorophenyl)-2-fluoro-4-methyl-2-pentene

生成物 1

HCID 540106844-(p-Chlorophenyl)-2-fluoro-1-(4-fluoro-3-phenoxyphenyl)-4-methyl-2-pentene収率 91%

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Under a nitrogen atmosphere, a mixture of 1-bromo-4-(p-chlorophenyl)-2-fluoro-4-methyl-2-pentene, (Z)- (320.8 mg, 1.1 mmol), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 31.6 mg, 0.055 mmol) in toluene (8 mL) is treated with potassium carbonate (608 mg, 4.4 mmol), degassed, treated with a solution of 4-fluoro-3-phenoxybenzeneboronic acid (331.8 mg, 1.43 mmol) in ethanol (2 mL), refluxed for 45 minutes, cooled to room temperature, and filtered through diatomaceous earth. The filtrate is diluted with ethyl acetate, and the resultant solution is washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexanes solution gives the title product as a colorless liquid (401 mg, 91% yield) which is identified by NMR spectral analyses.

後処理

  1. customdegassed
  2. temperaturerefluxed for 45 minutes
  3. filtrationfiltered through diatomaceous earth
  4. additionThe filtrate is diluted with ethyl acetate
  5. washthe resultant solution is washed sequentially with water and brine
  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-ee1e92e53e464c4ea860665476e2ccec
出典データセット
uspto-grants-1999_04
特許番号
US05892131

反応ノート

読み込み中…