Acetic Acid → N-[4-(2-Bromoacetyl)Phenyl]Acetamide

HRID 10786

Reaktionsgleichung

Reaktionsgleichung von HRID 10786
[Br:1]Br.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 24408BromineHCID 75937N-(p-acetylphenyl)acetamide

Produkt 1

HCID 12364739N-[4-(2-Bromoacetyl)Phenyl]AcetamideAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

A solution of bromine (0.31 mL, 5.9 mmol) in carbon tetrachloride (10 mL) was added to a suspension of N-(4-acetylphenyl)acetamide (1 g, 5.6 mmol) (Lancaster Synthesis) in carbon tetrachloride (20 mL). The reaction mixture was stirred for several hours but TLC indicated only starting material. Acetic acid (10 mL) was added, and the reaction mixture was stirred overnight. Filtration gave N-[4-(bromoacetyl)phenyl]acetamide (1.4 g) as a solid. HPLC indicated that the purity was approximately 80%. This material was used directly in subsequent steps without purification.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight
  2. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-f5d11cfe3cd8412daee3285f06654237
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094896B2

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