Anthraquinone → HCID 22138029, Verbindung

HRID 901744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901744
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].[CH:23]1[C:36]2[C:35](=[O:37])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:18]1[C:10]2[CH:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:35]4([OH:37])[C:34]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[C:28]([C:6]5[CH:7]=[CH:2][CH:3]=[C:4]([C:8]6[C:17]7[C:12]([C:11]8[CH:3]=[CH:2][CH:7]=[CH:6][C:10]=8[CH:9]=6)=[CH:13][CH:14]=[CH:15][CH:16]=7)[CH:5]=5)([OH:38])[C:27]5[C:36]4=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:7]=[CH:6][CH:5]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 6780AnthraquinoneHCID 25517Ammonium ChlorideHCID 221380473-(1-Naphthyl)-1-bromobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 22138029HCID 22138029, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, 1-(3-bromophenyl)naphthalene (6.5 g, 20 mmole, 2.8 eq) was dissolved into a mixed solvent composed of anhydrous toluene (25 ml) and anhydrous THF (25 ml) and the resultant solution was cooled at −25° C. in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.50 mole/liter, 15 ml, 23 mmole, 1.1 eq) was added and the resultant solution was stirred at −20° C. for 1 hour. To the obtained mixture, anthraquinone (1.5 g, 7.2 mmole) was added and the resultant mixture was stirred at −20° C. for 1 hour and at the room temperature for 3 hours and left standing for one night. To the obtained reaction mixture, a saturated aqueous solution of ammonium chloride (20 ml) was added. The formed solid was separated by filtration and washed with water, methanol and acetone and a white solid (5.9 g, quant.) was obtained.

Aufarbeitung

  1. waitleft
  2. waitstanding for one night
  3. customTo the obtained reaction mixture
  4. customThe formed solid was separated by filtration
  5. washwashed with water, methanol and acetone
  6. customa white solid (5.9 g, quant.) was obtained

Quellen und Nachweise

ORD-Eintrag
ord-8913b09266e8462a9a84c08f1a108f9d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361796B2

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