N-bromobutanimide → Methyl 2-amino-5-bromo-3-methoxybenzoate

HRID 249918

Reaktionsgleichung

Reaktionsgleichung von HRID 249918
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Br:21])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 602320Methyl 2-amino-3-methoxybenzoate

Produkt 1

HCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoateAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-amino-3-methoxybenzoate (13.0 g, 71.8 mmol) in DMF (30 mL) was added NBS (14.38 g, 80.8 mmol) at room temperature and the resulting reaction mixture was stirred for 17 h. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, 2% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-bromo-3-methoxybenzoate (13.7 g, 73%). 1H NMR consistent.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (silica gel, 2% to 5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d353f3eec5444e8a9d7627517f89b31a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

Verknüpfte Notizen

Wird geladen…