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Hydrochloric Acid → 1-(9-Anthryl)-4-(1-naphthyl)-naphthalene

HRID 431413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 431413
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[Mg].[CH:23]1[C:36]2[C:35](=O)[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.Cl>C(OCC)C.O1CCCC1>[CH:23]1[C:36]2[C:27](=[CH:28][C:29]3[C:34]([C:35]=2[C:15]2[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:12]([C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH:2]=[CH:3][CH:4]=4)=[CH:13][CH:14]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:25][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7018AnthroneHCID 5462224MagnesiumHCID 64258374-Bromo-1,1'-binaphthalene

Produkt 1

HCID 187610571-(9-Anthryl)-4-(1-naphthyl)-naphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-bromo-1,1′-binaphthyl and magnesium were refluxed in diethylether for one hour, which was then added to a solution of anthrone in tetrahydrofuran. The resulting mixture was heated for two hours, which was then poured into diluted hydrochloric acid. After being extracted by diethylether, organic layer was separated and dried over magnesium sulfate. It was purified according to conventional method, whereby 1-(9-anthryl)-4-(1-naphthyl)-naphthalene was obtained. This was dissolved in chloroform to which was added two equivalent amounts of N-bromosuccinimide, and they were stirred at room temperature for one day. The product was purified according to conventional method and 1-(10-bromo-9-anthryl)-4-(4-bromo-1-naphthyl)-naphthalene was obtained. With this pdoruct, diphenylamine was reacted in nitrobenzene at 180° C. for 40 hours together with potasium carbonate and copper powder. After nitrobenzene was removed by vacuum distillation, the reaction mixture was purified according to conventional method, whereby the target compound (18) was obtained.

Aufarbeitung

  1. temperatureThe resulting mixture was heated for two hours
  2. extractionAfter being extracted by diethylether, organic layer
  3. customwas separated
  4. dry with materialdried over magnesium sulfate
  5. customIt was purified

Quellen und Nachweise

ORD-Eintrag
ord-1701c653018c44508d919f3fef87ec1e
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06660408B1

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