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2-Bromothiophene → Fluorene

HRID 2209321
ノート
印刷プレビュー

反応式

HRID 2209321 の反応式
C(N1C2=CC3C(=CC2=C(C2SC(Br)=CC=2)C1=O)N(CCCCCC)C(=O)C=3C1SC(Br)=CC=1)CCCCC.CC1(C)C(C)(C)OB(C(CCCC)C[C:49]2[C:61]3[C:60](CC)(CC)[C:59]4[C:54](=[CH:55][CH:56]=[C:57](B5OC(C)(C)C(C)(C)O5)[CH:58]=4)[C:53]=3[CH:52]=[CH:51][CH:50]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].BrC1SC=CC=1>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.C1(C)C=CC=CC=1.O>[CH:49]1[C:61]2[CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:53]=2[CH:52]=[CH:51][CH:50]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 138512-BromothiopheneHCID 62657Potassium Phosphate, TribasicHCID 866982691,5-Dihexyl-3,7-di-(5-bromothiophen-2-yl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dioneHCID 866982702,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di-ethylhexylfluorene

生成物 1

HCID 6853Fluorene収率 372%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 22272177Toluene water溶媒

実験手順

A mixture of 1,5-Dihexyl-3,7-di-(5-bromothiophen-2-yl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (0.150 g, 0.221 mmol), 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di-ethylhexylfluorene (0.149 g, 0232 mmol), Pd2(dba)3 (5.0 mg), (o-tol)3P (3.0 mg), K3PO4 (0.187 g) and toluene/H2O (20 mL/1 mL) was heated at reflux for 24 h. 2-bromothiophene (0.035 g, 0.22 mmol) in toluene (1 mL) was added and the resulting mixture was stirred for another 12 h. Then, after cooling to room temperature, the mixture was dropped into methanol to precipitate. After being filtered and dried, the precipitation was Soxhlet extracted with methanol, acetone, hexane, dichloromethane and chloroform in succession. The chloroform solution was concentrated and reprecipitated in methanol. The solid was filtered and dried to yield polymer (0.165 g, 82.5%) as a blue-green solid.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customto precipitate
  4. filtrationAfter being filtered
  5. customdried
  6. customthe precipitation
  7. extractionextracted with methanol, acetone, hexane, dichloromethane and chloroform in succession
  8. concentrationThe chloroform solution was concentrated
  9. customreprecipitated in methanol
  10. filtrationThe solid was filtered
  11. customdried

出典と根拠

ORDレコード
ord-5217ef704d574976955f1011694a7d6a
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09379335B2

反応ノート

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