Hydrochloric Acid → (2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-one

HRID 2035382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2035382
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:5][CH:4]=1.[N:15]([O-])=[O:16].[Na+]>C1COCC1.C(OCC)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])/[C:10](=[N:15]\[OH:16])/[CH2:11][CH2:12][CH3:13])=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 817174'-BromovalerophenoneHCID 23668193Sodium Nitrite

Produkt 1

HCID 87519930(2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-oneAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The conc. HCl (40 mL) was added dropwise to a solution of 1-(4-bromophenyl)pentan-1-one (4.68 g, 19.41 mmol) and sodium nitrite (4.02 g, 58.2 mmol) in THF (80 ml) at 0° C. and allowed to warm to room temperature and stirred 18 hours. The reaction mixture was diluted with diethyl ether and the organic phase washed with sat'd NaHCO3 and brine. Concentration gave (Z)-1-(4-bromophenyl)-2-(hydroxyimino)pentan-1-one 3.1 g (33%) as an oil which was used without further purification.). RT=2.1 min, (Condition 1) LCMS: Anal. Calcd. for C11H12BrN1O2 270.01; found: 270.15 (M+H)+.

Aufarbeitung

  1. washthe organic phase washed with sat'd NaHCO3 and brine
  2. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-e76f12199c514967ac7046c5ac712fe8
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08574563B2

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