Potassium Carbonate → 3-(4-(9h-Carbazol-9-yl)phenyl)-9h-carbazole

HRID 41786

Reaktionsgleichung

Reaktionsgleichung von HRID 41786
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:15]1[C:27]2[N:26]([C:28]3[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:15]1[C:27]2[N:26]([C:28]3[CH:33]=[CH:32][C:31]([C:2]4[CH:3]=[CH:4][C:5]5[NH:6][C:7]6[C:12]([C:13]=5[CH:14]=4)=[CH:11][CH:10]=[CH:9][CH:8]=6)=[CH:30][CH:29]=3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2524463-BromocarbazoleHCID 231208274-(9H-Carbazol-9-yl)phenylboronic Acid

Produkt 1

HCID 593068843-(4-(9h-Carbazol-9-yl)phenyl)-9h-carbazoleAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5.0 g (20 mmol) of 3-bromo-9H-carbazole, 5.8 g (20 mmol) of 4-(9H-carbazol-9-yl)phenylboronic acid, and 308 mg (1.0 mmol) of tri(ortho-tolyl)phosphine were put into a 300 mL three-neck flask. The air in the flask was replaced with nitrogen. To the mixture were added 100 mL of ethyleneglycoldimethylether and 20 mL of an aqueous solution of potassium carbonate (2.0 mol/L). This mixture was stirred to be degassed under reduced pressure. After the degassing, 46 mg (0.20 mmol) of palladium(II) acetate was added the mixture. This mixture was refluxed at 90° C. for 4.5 hours. After the reflux, the organic layer of the mixture was washed with water twice, and the aqueous layer was extracted with acetate ether. The extract was combined with the organic layer and then washed with a saturated saline solution. The obtained organic layer was dried with magnesium sulfate. After the drying, the mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily light brown substance. The obtained oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of hexane:toluene=1:1) to give 5.4 g of a white powdered solid, which was the object of the synthesis, at a yield of 65%. A synthesis scheme of Step 3 is shown in (f-3) given below.

Aufarbeitung

  1. customto be degassed under reduced pressure
  2. washAfter the reflux, the organic layer of the mixture was washed with water twice
  3. extractionthe aqueous layer was extracted with acetate ether
  4. washwashed with a saturated saline solution
  5. dry with materialThe obtained organic layer was dried with magnesium sulfate
  6. filtrationAfter the drying, the mixture was subjected to gravity filtration
  7. customcondensed
  8. customto give an oily light brown substance
  9. customThe obtained oily substance was purified by silica gel column chromatography (a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-b880a6202fa14769a9dc2bf6a3a0676c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530672B2

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