Toluene → 4-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

HRID 1470895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470895
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[S:3]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:40][CH3:41])=[C:37]([Pb+3])[CH:38]=1>C(Cl)(Cl)Cl.ClCCl.Cl>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:40][CH3:41])=[C:35]([CH:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[S:3][C:4]([CH3:11])([CH3:10])[C:5]2=[O:9])[CH:34]=1

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 156501652,2,6,6-Tetramethylthiopyran-3,5-dioneHCID 178476533HCID 178476533, Verbindung

Produkt 1

HCID 684876664-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,2,6,6-tetramethylthiopyran-3,5-dione (prepared according to the procedure of E. Er and P. Margaretha, Helvetica Chimica Acta (1992), 75(7), 2265-69) (1.8 g, 9.9 mmol) and N,N-dimethylaminopyridine (5.3 g, 4.34 mmol) in chloroform (60 ml), is added toluene (18 ml) then 5-bromo-2-ethylphenyllead triacetate (6.2 g, 1.09 mmol) in one portion. The resulting mixture is heated at reflux for 2 hours, then allowed to cool to ambient temperature, diluted with dichloromethane and 1M aqueous hydrochloric acid, and the organic phase is separated. The organic phase is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio), giving 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione (2.42 g) as an orange solid.

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 hours
  3. customthe organic phase is separated
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio)

Quellen und Nachweise

ORD-Eintrag
ord-e812848443884fcf900638349d8468a6
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006429B2

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