Toluene → 6-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

HRID 1191583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191583
[CH3:1][C:2]1([CH3:13])[C:7](=[O:8])[C:6]([CH3:10])([CH3:9])[C:5](=[O:11])[CH2:4][C:3]1=[O:12].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:34][CH3:35])=[C:31]([Pb+3])[CH:32]=1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>ClCCl.Cl>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:34][CH3:35])=[C:29]([CH:4]2[C:3](=[O:12])[C:2]([CH3:13])([CH3:1])[C:7](=[O:8])[C:6]([CH3:9])([CH3:10])[C:5]2=[O:11])[CH:28]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6212ChloroformHCID 117691662,2,4,4-Tetramethylcyclohexane-1,3,5-trioneHCID 178476533HCID 178476533, Verbindung

Produkt 1

HCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trioneAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione (0.6 g, 3.6 mmol), 5-bromo-2-ethylphenyllead triacetate (2.27 g, 4.00 mmol) and N,N-dimethylaminopyridine (2.22 g, 18 mmol) is added anhydrous chloroform (25 ml) and toluene (6.3 ml), and the reaction mixture is heated at 80° C. for 3 hours. The mixture is diluted with dichloromethane (50 ml) and 2M aqueous hydrochloric acid (100 ml), and filtered through diatomaceous earth to remove inorganic residues. The filter cake is washed with dichloromethane, and all organic fractions are combined, washed with brine, dried over anhydrous magnesium sulphate then filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography to give 6-(5-bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione as a white solid (0.84 g).

Aufarbeitung

  1. filtrationfiltered through diatomaceous earth
  2. customto remove inorganic residues
  3. washThe filter cake is washed with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationthen filtered
  7. concentrationThe filtrate is concentrated in vacuo
  8. customthe residue is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ada384370f574beea59ba4eb76df9ff9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680012B2

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