Bromine → 2-Bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

HRID 731668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731668
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[C:15](=[O:17])[CH3:16])[CH2:3][CH2:2]1.[Br:18]Br>C(Cl)(Cl)(Cl)Cl.CC(O)=O>[Br:18][CH2:16][C:15]([C:5]1[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:7][O:8][C:4]=1[CH:1]1[CH2:3][CH2:2]1)=[O:17]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 674211361-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone

Produkt 1

HCID 247398072-Bromo-1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanoneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-ethanone (3.34 g, 14.6 mmol) in carbontetrachloride (9.7 mL) and AcOH (0.4 mL) at 48° C. was added a solution of bromine (0.79 mL, 14.6 mmol) in carbontetrachloride (7.8 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 (50 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 80:20) afforded the title compound (4.29 g, 95%) which was obtained as an off-white solid. MS m/e (EI): 305.0/307.0 [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 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-b2e60627a8294d0a8461175471cc4634
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585874B2

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