Hexane → 2-(3-Fluorophenyl)-dibenzo[f,h]quinoxaline

HRID 1253385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253385
CCCCCC.C([Li])CCC.Br[C:13]1[CH:14]=[C:15]([F:19])[CH:16]=[CH:17][CH:18]=1.[N:20]1[C:29]2[C:24](=[C:25]3[CH:37]=[CH:36][CH:35]=[CH:34][C:26]3=[C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]3=2)[N:23]=[CH:22][CH:21]=1>ClCCl.O.O1CCCC1>[F:19][C:15]1[CH:14]=[C:13]([C:22]2[CH:21]=[N:20][C:29]3[C:24](=[C:25]4[CH:37]=[CH:36][CH:35]=[CH:34][C:26]4=[C:27]4[CH:33]=[CH:32][CH:31]=[CH:30][C:28]4=3)[N:23]=2)[CH:18]=[CH:17][CH:16]=1

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 140821-Bromo-3-fluorobenzeneHCID 252644Dibenzo(f,h)quinoxalineHCID 178418339Butyllithium

Produkt 1

HCID 577301122-(3-Fluorophenyl)-dibenzo[f,h]quinoxalineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

First, under a nitrogen atmosphere, 27.5 mL (1.58 mol/L) of a hexane solution of n-butyllithium was dripped into a mixed solution of 6.87 g of 3-bromofluorobenzene and 40 mL of tetrahydrofuran at −78° C. Then, with the temperature maintained at −78° C., the mixture was stirred for 2 hours. To the obtained solution was added 7.54 g of dibenzo[f,h]quinoxaline in five additions at −78° C. The mixture was heated to room temperature,and stirred for 12 hours with the temperature maintained at room temperature. Water was added to this mixture and dichloromethane was used as an extraction solvent, so that an organic layer was extracted. The obtained organic layer was dried with anhydrous magnesium sulfate. The solution obtained by the drying was filtrated. The solvent of this solution was distilled off, and then, by recrystallization with ethanol, the organometallic complex of the present invention, Hdbq-3FP, which was the target substance, was obtained (a light-orange powder, yield: 23%). Synthesis scheme of Step 1 is shown in (a-2) below.

Aufarbeitung

  1. temperatureThe mixture was heated to room temperature
  2. stirringstirred for 12 hours with the temperature
  3. temperaturemaintained at room temperature
  4. extractionwas extracted
  5. dry with materialThe obtained organic layer was dried with anhydrous magnesium sulfate
  6. customThe solution obtained by the drying
  7. filtrationwas filtrated
  8. distillationThe solvent of this solution was distilled off
  9. customby recrystallization with ethanol
  10. customwas obtained (a light-orange powder, yield: 23%)
  11. customSynthesis scheme of Step 1

Quellen und Nachweise

ORD-Eintrag
ord-9ce8d8eff8144a85b70142db6700de48
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455111B2

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