4,4'-Dibromobenzophenone → HCID 58085476, Verbindung

HRID 923703

Reaktionsgleichung

Reaktionsgleichung von HRID 923703
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.C([Li])CCC.[Br:26][C:27]1[CH:41]=[CH:40][C:30]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=2)=O)=[CH:29][CH:28]=1>O1CCCC1.C(O)(=O)C.S(=O)(=O)(O)O>[Br:26][C:27]1[CH:41]=[CH:40][C:30]([C:31]2([C:33]3[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][CH:34]=3)[C:19]3[C:20]4=[C:15]([C:14]5[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=5[N:8]4[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=4)[CH:16]=[CH:17][CH:18]=3)=[CH:29][CH:28]=1

Komponenten

7

Edukt 3

HCID 728684,4'-DibromobenzophenoneHCID 594650129-(2-Bromophenyl)-9H-carbazoleHCID 178418339Butyllithium

Produkt 1

HCID 58085476HCID 58085476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1118Sulfuric AcidKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

6.96 g of 9-(2-bromophenyl)-9H-carbazole as the intermediate of Preparation Example 8 was dissolved in 10 mL of purified tetrahydrofuran, and the resulting solution was cooled to −78° C. and 8.64 mL of butyllithium was slowly added dropwise. The mixture was stirred at the same temperature for 30 min, and 6.12 g of 4,4′-dibromobenzophenone was added. The mixture was stirred at the same temperature for 40 min and then further stirred at room temperature for an additional 3 hours. The reaction was terminated with aqueous ammonium chloride, and the reaction mixture was extracted with ethyl ether. The organic layer was dewatered using anhydrous magnesium sulfate, and the organic solvent was then removed. The resulting solid was dispersed in ethanol, stirred for one day, filtered, and vacuum dried, thus obtaining an intermediate material. The solid thus obtained was dispersed in 10 mL of acetic acid, and 10 drops of concentrated sulfuric acid were added, after which the mixture was refluxed for 4 hours. The resulting solid was filtered, washed with ethanol, and vacuum dried, yielding a 8,8-bis(4-bromophenyl)-8H-indolo[3,2,1-de]acridine compound.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 40 min
  2. stirringfurther stirred at room temperature for an additional 3 hours
  3. customThe reaction was terminated with aqueous ammonium chloride
  4. extractionthe reaction mixture was extracted with ethyl ether
  5. customthe organic solvent was then removed
  6. additionThe resulting solid was dispersed in ethanol
  7. stirringstirred for one day
  8. filtrationfiltered
  9. customvacuum dried
  10. customthus obtaining an intermediate material
  11. customThe solid thus obtained
  12. temperatureafter which the mixture was refluxed for 4 hours
  13. filtrationThe resulting solid was filtered
  14. washwashed with ethanol, and vacuum
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-abab07763426470c85969a09c21cd31b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278986B2

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