Hydrogen Bromide → N-[2-(2-bromoacetyl)phenyl]acetamide

HRID 1072519

Reaktionsgleichung

Reaktionsgleichung von HRID 1072519
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].[BrH:14].BrBr>C(O)(=O)C>[Br:14][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])=[O:3]

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 21306N-(2-Acetylphenyl)acetamideHCID 24408Bromine

Produkt 1

HCID 2749459N-[2-(2-bromoacetyl)phenyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

31 g (0.175 mol) of N-(2-Acetylphenyl)-acetamide (prepared by acylation of 2-aminoacetophenone with acetyl chloride as described by Fuerstner, Alois; Jumbam, Denis N.; Tetrahedron; 48; 29; 5991-6010, (1992)) was dissolved in 200 ml of glacial acetic acid. 127 ml of 33% strength HBr in glacial acetic acid was added and then, at room temperature, 8.75 ml (0.175 mol) of bromine was slowly run in. The mixture was stirred at room temperature overnight. The mixture was stirred into 1.5 l of ice-water, and the precipitated product was filtered off with suction, thoroughly washed with ice-water and dried in vacuo. The crude product contained, according to HPLC and NMR, some precursor and dibrominated product, but was pure enough (about 85% strength) for further reaction.

Aufarbeitung

  1. customat room temperature
  2. filtrationthe precipitated product was filtered off with suction
  3. washthoroughly washed with ice-water
  4. customdried in vacuo
  5. customfor further reaction

Quellen und Nachweise

ORD-Eintrag
ord-686afb02858343efb828dce89b6416af
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911453B2

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