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Bromine → 2-Bromo-1-(3-phenyl-1,2-oxazol-4-yl)ethan-1-one

HRID 2219300
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2219300
[C:1]1([C:7]2[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br>C(Cl)(Cl)Cl.CC(O)=O>[Br:15][CH2:13][C:12]([C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][O:9][CH:10]=1)=[O:14]
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Komponenten

5

Edukt 2

HCID 24408BromineHCID 13196485Ethanone, 1-(3-phenyl-4-isoxazolyl)-

Produkt 1

HCID 599496022-Bromo-1-(3-phenyl-1,2-oxazol-4-yl)ethan-1-oneAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(3-phenyl-isoxazoi-4-yl)-ethanone (6.35 g, 34 mmol) in chloroform (50 mL) and AcOH (1 mL) at 48° C. was added a solution of bromine (1.83 mL, 36 mmol) in chloroform (15 mL) over 10 min keeping the temperature below 50° C. After addition the reaction mixture was allowed to cool down to room temperature and poured into ice-water (200 mL). The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were then washed with water and brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 7:3) afforded the title compound (3.72 g, 41%) which was obtained as a light yellow solid. MS m/e (EI): 265.0/267.0 [M].

Aufarbeitung

  1. customthe temperature below 50° C
  2. additionAfter addition the reaction mixture
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane
  5. washThe combined organic layers were then washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-d6b63fa91f614db390451c6a1786b685
Quelldatensatz
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07414061B2

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