Potassium Carbonate → 9-(4'-(8-bromodibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole

HRID 1486379

Reaktionsgleichung

Reaktionsgleichung von HRID 1486379
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:33]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:27]5[C:22]4=[CH:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)O1.Br[C:36]1[CH:49]=[CH:48][C:39]2[O:40][C:41]3[CH:46]=[CH:45][C:44]([Br:47])=[CH:43][C:42]=3[C:38]=2[CH:37]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:47][C:44]1[CH:45]=[CH:46][C:41]2[O:40][C:39]3[CH:48]=[CH:49][C:36]([C:9]4[CH:10]=[CH:11][C:12]([C:15]5[CH:16]=[CH:17][C:18]([N:21]6[C:22]7[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=7[C:28]7[C:33]6=[CH:32][CH:31]=[CH:30][CH:29]=7)=[CH:19][CH:20]=5)=[CH:13][CH:14]=4)=[CH:37][C:38]=3[C:42]=2[CH:43]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 822902,8-DibromodibenzofuranHCID 582992689-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole

Produkt 1

HCID 1176072519-(4'-(8-bromodibenzo[b,d]furan-2-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazoleAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 9-(4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (1.75 g, 4.42 mmol), 2,8-dibromodibenzo[b,d]furan (2.52 g, 7.74 mmol), tetrakis(triphenylphosphine) palladium(0) (0.25 g, 0.22 mmol), potassium carbonate (1.83 g, 13.26 mmol), 1,4-dioxane (40.00 mL), and water (8.00 mL) was degassed with bubbling argon for 30 minutes. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 15 (1.09 g, 44%). Confirmed by LCMS (APCI): calculated for C36H22BrNO (M+H): 564. Found: 564.

Aufarbeitung

  1. customwas degassed with bubbling argon for 30 minutes
  2. temperaturemaintaining an argon atmosphere
  3. customConsumption of the starting material
  4. temperaturethe reaction was cooled to room temperature
  5. extractionThe product was extracted with dichloromethane
  6. customdried
  7. custompurified by silica gel column chromatography with dichloromethane in hexanes as the eluent
  8. customThe product fractions were then dried
  9. customthe product was collected

Quellen und Nachweise

ORD-Eintrag
ord-9d3211ca6b0e45888f2a83ff6903a7c0
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09425408B2

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