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2-Bromothiophene → Fluorene

HRID 2209321
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HRID 2209321 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 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

생성물 1

HCID 6853Fluorene수율 372%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 22272177Toluene water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5217ef704d574976955f1011694a7d6a
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09379335B2

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