Water → 2-Bromo-1-(4-tert-butylphenyl)ethan-1-one

HRID 576059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576059
[BrH:1].Br.Br.N1CCCC1=O.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].O>O1CCCC1>[Br:1][CH2:21][C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:10]([CH3:13])([CH3:11])[CH3:12])=[CH:19][CH:18]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 962WaterHCID 13669p-tert-ButylacetophenoneHCID 20283272Pyrrolidone trihydrobromide

Produkt 1

HCID 23247702-Bromo-1-(4-tert-butylphenyl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Pyrrolidone trihydrobromide (3.27 g, 10.0 mmol) was added to a solution of 1-(4-tert-butylphenyl)ethanone obtained (1.61 g, 9.13 mmol) in tetrahydrofuran (30 mL) and the mixture was heated to an external temperature of 60° C. and stirred for 30 min. After cooling, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a colorless oil (472 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Quellen und Nachweise

ORD-Eintrag
ord-f1f4f4e3c8d547a386e2a72372f8552e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035059B2

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