m-Nitroacetophenone → 2-Bromo-1-(3-nitrophenyl)ethan-1-one

HRID 45674

Reaktionsgleichung

Reaktionsgleichung von HRID 45674
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:13]Br>C(O)(=O)C>[Br:13][CH2:11][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 8494m-NitroacetophenoneHCID 24408Bromine

Produkt 1

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Into a 500-mL 3-necked round-bottom flask, was placed a solution of 1-(3-nitrophenyl)ethanone (50 g, 303.03 mmol, 1.00 equiv) in acetic acid (300 mL), Br2 (53.5 g, 331.6 mmol, 1.00 equiv). The resulting solution was stirred for 2 h at 60° C. in an oil bath. The reaction was then quenched by the addition of ice and the solids were collected by filtration. The crude product was re-crystallized from ethyl acetate/petroleum ether in the ratio of 1:10. This resulted in 25 g (34%) of 2-bromo-1-(3-nitrophenyl)ethanone as a white solid.

Aufarbeitung

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of ice
  3. filtrationthe solids were collected by filtration
  4. customThe crude product was re-crystallized from ethyl acetate/petroleum ether in the ratio of 1:10
  5. customThis resulted in 25 g (34%) of 2-bromo-1-(3-nitrophenyl)ethanone as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-87d622e1cc0d44ee93fb79047803f5d7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541448B2

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