N-bromobutanimide → Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

HRID 1158062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158062
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>CC#N.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>[Br:14][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 11651240Ethyl 2-(pyridin-4-yl)propanoate

Produkt 1

HCID 58930190Ethyl 2-bromo-2-(pyridin-4-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

The above compounds were prepared according to the procedure reported in the literature: see D. Yang, J. Org. Chem. 2002, 67, 7429. MS: 258, 260 (M+1). To a solution of ethyl 2-(pyridin-4-yl)propanoate (5.3 g, 30 mmol), Mg(ClO4)2 (Aldrich, 2.0 g, 9.0 mmol) in CH3CN (60 mL) was added N-bromosuccinimide (Aldrich, 5.9 g, 33 mmol) at room temperature. After 2 h, the reaction mixture was diluted with ether (200 mL), and 10% Na2CO3. The organic phase was separated, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography. Mass Spec. m/z+ion 258, 260 (M+1).

Aufarbeitung

  1. customThe above compounds were prepared
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-efdfa81e5cb045128751cbbed9a88695
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807700B2

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