2-Bromothiophene → Diketopyrrolopyrrole

HRID 2209324노트

반응식

HRID 2209324 반응식
C(N1C2=CC3C(=CC2=C(C2SC(Br)=CC=2)C1=O)N(CCCCCC)C(=[O:25])C=3C1SC(Br)=CC=1)CCCCC.C(C(CCCCCCCCCC)C[N:49]1[C:56](C2SC(B3OC(C)(C)C(C)(C)O3)=CC=2)=[C:55]2[C:51](=[C:52](C3SC(B4OC(C)(C)C(C)(C)O4)=CC=3)[N:53](CC(CCCCCCCC)CCCCCCCCCC)[C:54]2=[O:71])[C:50]1=O)CCCCCCC.[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].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.CO.C1(C)C=CC=CC=1.O>[O:25]=[C:55]1[C:56]2[C:52]([CH:51]=[CH:50][N:49]=2)=[N:53][C:54]1=[O:71]

참가 물질

10

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 866982722,5-Bis(2-octyldodecyl)-3,6-bis(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

생성물 1

HCID 23363597Diketopyrrolopyrrole수율 705.4%

시약·촉매·용매 5

HCID 2734635Tri-tert-butylphosphine tetrafluoroborate촉매HCID 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 (0.100 g, 0.148 mmol), 2,5-dihydro-2,5-bis(2-octyldodecyl)-3,6-bis[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]-pyrrolo[3,4-c]pyrrole-1,4-dione (0.168 g, 0.150 mmol), Pd2(dba)3 (4.0 mg), tri-tert-butylphosphonium tetrafluoroborate (2.0 mg), K3PO4 (0.095 g) and toluene/H2O (8 mL/0.3 mL) was heated at reflux for 48 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 (0.14 g, 70%) as a black solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 48 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-8ce89456b51e4331ab17b2a31360e1db
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09379335B2

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