Toluene → 4-(5-Bromo-2-chlorophenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 1470878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470878
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[O:3]1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:36][C:37]1[CH:38]=[CH:39][C:40]([Cl:44])=[C:41]([Pb+3])[CH:42]=1>ClCCl.Cl>[Br:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:44])=[C:39]([CH:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[O:3][C:4]([CH3:11])([CH3:10])[C:5]2=[O:9])[CH:38]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6212ChloroformHCID 199092752,2,6,6-Tetramethyloxane-3,5-dioneHCID 178476543[Diacetyloxy-(5-bromo-2-chlorophenyl)plumbyl] acetate

Produkt 1

HCID 684878854-(5-Bromo-2-chlorophenyl)-2,2,6,6-tetramethylpyran-3,5-dioneAusbeute 7,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2,2,6,6-tetramethylpyran-3,5-dione (2.78 g, 16.3 mmol) and N,N-dimethylaminopyridine (9.97 g, 81.6 mmol) is added anhydrous chloroform (120 ml). To this solution is added anhydrous toluene (30 ml), followed by 5-bromo-2-chlorophenyllead triacetate (10.32 g, 18 mmol) in one portion and the reaction mixture is heated at 80° C. overnight. The mixture is allowed to cool to room temperature, then diluted with dichloromethane (120 ml) and 2M aqueous hydrochloric acid (250 ml), followed by filtration through diatomaceous earth to remove inorganic residues. The filter cake is washed with dichloromethane, and all organic fractions are combined, washed with 2M hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate then concentrated in vacuo. This material is finally purified by flash column chromatography on silica gel to afford 4-(5-bromo-2-chlorophenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.44 g) of sufficient purity to use directly in the next step.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfollowed by filtration through diatomaceous earth
  3. customto remove inorganic residues
  4. washThe filter cake is washed with dichloromethane
  5. washwashed with 2M hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthen concentrated in vacuo
  8. customThis material is finally purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-45c50dba1e324181b3463c018d2eb863
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006429B2

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