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Potassium Carbonate → 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene

HRID 924544
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 924544
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[CH:18]1[C:26]2[C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[S:23][C:22]=2[CH:21]=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Br:15][C:8]1[CH:7]=[C:6]2[C:11]([C:12]3[CH:13]=[CH:14][C:2]([C:28]4[CH:29]=[CH:30][C:24]5[S:23][C:22]6[CH:21]=[CH:20][CH:19]=[CH:18][C:26]=6[C:25]=5[CH:27]=4)=[CH:3][C:4]=3[C:5]2([CH3:16])[CH3:17])=[CH:10][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2794660Dibenzothiophene-2-boronic AcidHCID 121238762,7-Dibromo-9,9-dimethylfluorene

Produkt 1

HCID 902619402-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiopheneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

2,7-dibromo-9,9-dimethyl-9H-fluorene (5.0 g, 14.201 mmol), dibenzo[b,d]thiophen-2-ylboronic acid (1.62 g, 7.10 mmol), Pd(pph3)4 (820 mg, 0.71 mmol), K2CO3 (1.96 g, 14.201 mmol) were put in a 250 mL two-neck flask and dissolved in toluene/H2O. The solution was refluxed and stirred for 12 hours. After completion of the reaction, the solution was distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of hexane and methylenechloride (9:1). The solution was distilled under reduced pressure and was re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound was obtained, (1.61 g, yield: 50%).

Aufarbeitung

  1. temperatureThe solution was refluxed
  2. customAfter completion of the reaction
  3. distillationthe solution was distilled under reduced pressure
  4. customto remove the solvent
  5. distillationThe solution was distilled under reduced pressure
  6. customwas re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound
  7. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-a95883f0156743c19dc99768c7a15e78
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09281482B2

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