Hydrochloric Acid → 4-Nitrobenzoylacetonitrile

HRID 1860514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860514
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].[C-:14]#[N:15].[Na+].Cl>C(O)C.O>[C:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4])#[N:15]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 668402-Bromo-4'-nitroacetophenone

Produkt 1

HCID 5914594-Nitrobenzoylacetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-bromo-4′-nitroacetophenone (30 g, 0.123 mol) in ethanol (200 mL) at 0° C. was added a solution of NaCN (18 g, 0.368 mol) in H2O (60 mL) dropwise over 1 h. Upon completion of the addition, the mixture was stirred at 0° C. for an additional hour and then diluted with H2O (200 mL). The solution was treated with 1N aq. HCl solution, to a pH of 2, and extracted with CH2Cl2 (2×500 ML). The combined organic layers were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc to obtain 2-cyano-4′nitroacetophenone as an orange solid.

Aufarbeitung

  1. additionUpon completion of the addition
  2. extractionextracted with CH2Cl2 (2×500 ML)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e56148dc6f2d4fbf9891222ab662e938
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531478B2

Notizen zur Reaktion

Wird geladen…