Hydrochloric Acid → 4-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 341660

Reaktionsgleichung

Reaktionsgleichung von HRID 341660
[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.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([Pb+3])=[C:32]([CH2:37][CH3:38])[CH:31]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([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])=[C:32]([CH2:37][CH3:38])[CH:31]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 199092752,2,6,6-Tetramethyloxane-3,5-dioneHCID 178476529HCID 178476529, Verbindung

Produkt 1

HCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dioneAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,2,6,6-Tetramethylpyran-3,5-dione (8 g, 0.047 mol) and 4-dimethylaminopyridine (24 g, 0.196 mol) are added to a mixture of chloroform (160 ml) and toluene (40 ml). The reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4-Bromo-2-ethyl-phenyllead triacetate (29.4 g, 0.051 mol) is added in one portion and the reaction mixture is stirred and heated to 80° C. (pre-heated oil bath) under an atmosphere of nitrogen for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered through a plug of diatomaceous earth and the two phases are separated. The aqueous phase is extracted with dichloromethane (2×100 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione as a white solid (10 g).

Aufarbeitung

  1. customThe reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature
  2. temperature(pre-heated oil bath) under an atmosphere of nitrogen for 1 hour
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through a plug of diatomaceous earth
  5. customthe two phases are separated
  6. extractionThe aqueous phase is extracted with dichloromethane (2×100 ml)
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe mixture is filtered
  10. customthe filtrate is evaporated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d22627d491c345e2b4f3fd1baebde985
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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