Acetylpyrazine → 2-Bromo-1-pyrazin-2-yl-ethanone

HRID 1766212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766212
[C:1]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Br-:10].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:10][CH2:2][C:1]([C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1)=[O:3]

Komponenten

4

Edukt 2

HCID 30914AcetylpyrazineHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 158231122-Bromo-1-pyrazin-2-yl-ethanoneAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Acetylpyrazine (244 mg, 2.0 mmol) was suspended in glacial acetic acid (10 mL) and treated with pyridinium tribromide (640 mg, 2.0 mmol). The reaction mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with 1:1 hexane/ethyl acetate, to provide 2-(2-bromoacetyl)pyrazine as a brown solid (154 mg, 38%). 1H NMR (200 MHz, DMSO-d6) δ 9.16 (d, J=1.5 Hz, 1H), 8.94 (d, J=2.4 Hz, 1H), 8.82 (dd, J=1.5, 2.4 Hz, 1H), 4.99 (s, 2H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 1:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d0209c386f9c40c29d6639a095b85538
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230019B2

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