Hydroxyamine hydrochloride → 8-Bromo-5,6-difluoro-2,3-dihydrochromen-4-one oxime

HRID 1363195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363195
[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]([F:13])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C:7]2=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:14])[C:5]([F:13])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C:7]2=[N:16][OH:17]

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 669706288-Bromo-5,6-difluorochroman-4-one

Produkt 1

HCID 866101588-Bromo-5,6-difluoro-2,3-dihydrochromen-4-one oximeAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 8-bromo-5,6-difluoro-2,3-dihydrochromen-4-one (7.2 mmol) in 40 mL of ethanol was added hydroxylamine hydrochloride (0.55 g, 7.9 mmol) and sodium acetate (0.65 g, 7.9 mmol). This mixture heated at reflux for 20 hrs. The mixture was cooled, diluted with EtOAc, washed with water and brine, and then dried over Na2SO4. Concentration of the solvent provided the title compound as a white solid (1.9 g). 1H NMR (300 MHz, 10% CD3OD in CDCl3): δ 7.3 (t, 1H), 4.2 (t, 2H), 2.9 (t, 2H).

Aufarbeitung

  1. temperatureThis mixture heated
  2. temperatureat reflux for 20 hrs
  3. temperatureThe mixture was cooled
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-4249289ae336456ca75101df126c97c7
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884109B2

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