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Potassium Carbonate → 2-{3-[3-(Dibenzothiophen-4-yl)phenyl]phenyl}dibenzo[f,h]quinoline

HRID 626606
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Reaktionsgleichung

Reaktionsgleichung von HRID 626606
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]4[CH:25]=[CH:24][CH:23]=[CH:22][C:12]4=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:26]1[C:34]2[C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[S:31][C:30]=2[C:29]([C:39]2[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=2)=[CH:28][CH:27]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C1(C)C=CC=CC=1.O.C(O)C>[CH:26]1[C:34]2[C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[S:31][C:30]=2[C:29]([C:39]2[CH:40]=[C:41]([C:2]3[CH:3]=[C:4]([C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[C:11]6[CH:25]=[CH:24][CH:23]=[CH:22][C:12]6=[C:13]6[CH:21]=[CH:20][CH:19]=[CH:18][C:14]6=5)[N:9]=4)[CH:5]=[CH:6][CH:7]=3)[CH:42]=[CH:43][CH:44]=2)=[CH:28][CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 58261920(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)boronic acidHCID 866755632-(3-Bromophenyl)dibenzo[f,h]quinoline

Produkt 1

HCID 866755622-{3-[3-(Dibenzothiophen-4-yl)phenyl]phenyl}dibenzo[f,h]quinolineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel

5
HCID 167845palladium(II) acetateKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

In a 50-mL three-neck flask, 0.56 g (1.5 mmol) of 2-(3-bromophenyl)dibenzo[f,h]quinoline, 0.46 g (1.5 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 58 mg (0.19 mmol) of tri(ortho-tolyl)phosphine, 15 mL of toluene, 1.5 mL of ethanol, and 1.5 mL of a 2M aqueous solution of potassium carbonate were put. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. Then, 17 mg (77 μmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80° C. for 9 hours under a nitrogen stream. After a predetermined time, water and toluene were added to this mixture, and the resulting solid was collected by suction filtration. A toluene solution of the obtained solid was suction-filtered through alumina and Celite, and the filtrate was concentrated to give a yellow solid. A methanol suspension of the obtained solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that the object of the synthesis was obtained as 0.52 g of white powder in 63% yield.

Aufarbeitung

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred at 80° C. for 9 hours under a nitrogen stream
  3. filtrationthe resulting solid was collected by suction filtration
  4. filtrationA toluene solution of the obtained solid was suction-filtered through alumina and Celite
  5. concentrationthe filtrate was concentrated
  6. customto give a yellow solid
  7. customwas irradiated with ultrasonic waves
  8. filtrationa solid was collected by suction filtration, so that the object of the synthesis

Quellen und Nachweise

ORD-Eintrag
ord-f9033963dc924b349ea16896d18172f4
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309223B2

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