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Bromobenzene → 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 40404
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 40404
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22](=[O:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29](=[O:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37].[CH2:39]1COC[CH2:40]1>>[Br:13][C:14]1[CH:15]=[C:16]2[C:34](=[CH:35][CH:36]=1)[C:19]1=[CH:20][C:21]3[C:22]([C:9]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:10]=4)([OH:33])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[C:29]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)([OH:32])[C:30]=3[CH:31]=[C:18]1[C:17]2([CH3:38])[CH3:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 581753612-Bromo-13,13-dimethyl-6H-indeno(1,2-b)anthracene-6,11(13H)-dioneHCID 178418339Butyllithium

Produkt 1

HCID 673870832-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diolAusbeute 82 %

Versuchsvorschrift

Bromobenzene (8.5 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 −78□, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 2-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (10 g, 0.024 mol) was added and the reaction mixture was stirred at room temperature for 17 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 2-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (11 g, yield=82%).

Aufarbeitung

  1. additionwas gradually added at −78□, and the reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature for 17 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-c075f70a111f43b0b457dcd343c71a4b
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08525158B2

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