Dimethylformamide → Methyl 4-acetamido-5-bromo-2-hydroxybenzoate

HRID 17537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17537
[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:28])[C:21](=[CH:26][CH:27]=1)[C:22]([O:24][CH3:25])=[O:23])(=[O:16])[CH3:15]>C(OCC)(=O)C>[C:14]([NH:17][C:18]1[CH:19]=[C:20]([OH:28])[C:21](=[CH:26][C:27]=1[Br:1])[C:22]([O:24][CH3:25])=[O:23])(=[O:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 77719Methyl 4-acetamidosalicylate

Produkt 1

HCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

N-Bromosuccinimide (0.94 g, 5.3 mmol) was added to an N,N-dimethylformamide (8 ml) solution of methyl 4-acetylaminosalicylate (I-248) (1.1 g, 5.0 mmol), followed by stirring with heating under reflux at 70 to 75° C. for 2 hours and a half. After cooling to room temperature, ethyl acetate was added, followed by washing twice with saturated brine and drying over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform/methanol (100:1) gave the entitled compound (0.64 g, 45%) as a pale red solid.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureAfter cooling to room temperature
  3. washby washing twice with saturated brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cd8d1709fc024f3a9cf523ecc46a0a6f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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