Hydroxyamine hydrochloride → (NE)-N-[(4-bromo-2,5-difluorophenyl)methylidene]hydroxylamine

HRID 516548

Reaktionsgleichung

Reaktionsgleichung von HRID 516548
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.Cl.[OH:13][NH2:14]>N1C=CC=CC=1.C(O)C.[Cl-].[NH4+]>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5](/[CH:6]=[N:14]/[OH:13])=[C:4]([F:11])[CH:3]=1

Komponenten

6

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 224890814-Bromo-2,5-difluorobenzaldehyde

Produkt 1

HCID 90310471(NE)-N-[(4-bromo-2,5-difluorophenyl)methylidene]hydroxylamineAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1049PyridineLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-2,5-difluorobenzaldehyde (7.0 g, 31.67 mmol), hydroxyl amine hydrochloride (2.42 g, 34.84 mmol) in pyridine (35 mL) and ethanol (35 mL) was stirred at room temperature for 30 min. The reaction mixture was diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with saturated brine solution, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, eluting with 5-100% ethyl acetate in hexanes) to provide the title compound as a yellow solid (4.0 g, 53%): ESIMS m/z 238 [(M+2H)+].

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated brine solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (SiO2, eluting with 5-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2b742c3ec23b4560b2f4e16afbf75d16
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09113629B2

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