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

HRID 2262527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262527
[C:1]1([C:7]2[C:11]([C:12](=[O:14])[CH3:13])=[C:10]([C:15]([F:18])([F:17])[F:16])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:19]Br>C(Cl)(Cl)Cl.CC(O)=O>[Br:19][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][C:10]=1[C:15]([F:17])([F:18])[F:16])=[O:14]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 673634031-(3-Phenyl-5-trifluoromethyl-isoxazol-4-yl)-ethanone

Produkt 1

HCID 873703972-Bromo-1-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-ethanoneAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-ethanone (2.88 g, 11 mmol) in chloroform (11 mL) and AcOH (0.6 mL) at 48° C. was added a solution of bromine (0.61 mL, 12 mmol) in chloroform (3.5 mL) over 5 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 4:1) afforded the title compound (2.2 g, 59%) which was obtained as a light yellow oil. MS: m/e=334.3/336.4 [M+H]+.

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 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c40529d311e454db32dab8bf2b968e5
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851469B2

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