9-Bromophenanthrene → HCID 86657206, Verbindung

HRID 40412

Reaktionsgleichung

Reaktionsgleichung von HRID 40412
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li][CH2:17][CH2:18][CH2:19][CH3:20].[Br:21][C:22]1[CH:35]=[CH:34][C:33]2[C:32](=[O:36])[C:31]3[CH:30]=[C:29]4[C:37]5[C:42]([C:43]([CH3:45])([CH3:44])[C:28]4=[CH:27][C:26]=3[C:25](=[O:46])[C:24]=2[CH:23]=1)=[CH:41][CH:40]=[CH:39][CH:38]=5>C1COCC1>[Br:21][C:22]1[CH:35]=[CH:34][C:33]2[C:32]([C:2]3[C:3]4[C:8]([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[CH:15]=3)=[CH:7][CH:6]=[CH:5][CH:4]=4)([OH:36])[C:31]3[CH:30]=[C:29]4[C:37]5[C:42]([C:43]([CH3:44])([CH3:45])[C:28]4=[CH:27][C:26]=3[C:25]([C:18]3[C:19]4[C:20]([C:2]6[CH:15]=[CH:14][CH:9]=[CH:8][C:3]=6[CH:17]=3)=[CH:7][CH:6]=[CH:5][CH:4]=4)([OH:46])[C:24]=2[CH:23]=1)=[CH:41][CH:40]=[CH:39][CH:38]=5

Komponenten

5

Edukt 3

HCID 113099-BromophenanthreneHCID 58175293HCID 58175293, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 86657206HCID 86657206, VerbindungAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

9-bromophenanthrene (13.88 g, 0.054 mol) was placed in a flask, and THF (200 ml) was added thereto. After dissolution, n-BuLi (38.4 ml, 0.06 mol) was gradually added at −780, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 9-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (9.67 g, 0.024 mol) was added and the reaction mixture was stirred at room temperature for 12 hours. After the reaction was terminated, the reaction solution was washed with distilled water, extracted with ethyl acetate, and purified by column chromatography to give 9-bromo-13,13-dimethyl-6,11-di(phenanthren-9-yl)-11,13-dihydro6H-indeno[1,2-b]anthracene-6,11-diol (11.7 g, yield=64%).

Aufarbeitung

  1. additionwas gradually added at −780
  2. stirringthe reaction mixture was stirred at room temperature for 12 hours
  3. customAfter the reaction was terminated
  4. washthe reaction solution was washed with distilled water
  5. extractionextracted with ethyl acetate
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d09c11998eef444088b4328b3090a3c8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08525158B2

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