Potassium Carbonate → 3-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole

HRID 1486380

Reaktionsgleichung

Reaktionsgleichung von HRID 1486380
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:24]1[CH:37]=[CH:36][C:27]2[O:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[C:26]=2[CH:25]=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:35][C:32]1[CH:33]=[CH:34][C:29]2[O:28][C:27]3[CH:36]=[CH:37][C:24]([C:16]4[CH:17]=[CH:18][C:19]5[N:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[C:8]6[C:13]([C:14]=5[CH:15]=4)=[CH:12][CH:11]=[CH:10][CH:9]=6)=[CH:25][C:26]=3[C:30]=2[CH:31]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 822902,8-DibromodibenzofuranHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Produkt 1

HCID 706610833-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazoleAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (9-phenyl-9H-carbazol-3-yl)boronic acid (1.50 g, 5.22 mmol), 2,8-dibromodibenzo[b,d]furan (2.98 g, 9.14 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.17 g, 15.67 mmol), 1,4-dioxane (50.00 mL), and water (10.00 mL) was degassed with bubbling argon for 30 min. 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 17 (1.65 g, 65%). Confirmed by LCMS (APCI): calculated for C30H18BrNO (M+H): 488. Found: 488.

Aufarbeitung

  1. customwas degassed with bubbling argon for 30 min
  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-e2c77f4bc16c48b99a9dd32cd7a8ae87
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09425408B2

Verknüpfte Notizen

Wird geladen…