Ethyl Acetate → 2-(2-Bromoacetyl)-6-nitro-benzoic acid methyl ester

HRID 2251861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251861
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH3:14].[Br:17]C1(Br)C(=O)NC(=O)NC1=O.CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:15])[CH2:14][Br:17]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 948775,5-Dibromobarbituric acidHCID 59644399Methyl 2-acetyl-6-nitrobenzoate

Produkt 1

HCID 596443972-(2-Bromoacetyl)-6-nitro-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The mixture of 2-acetyl-6-nitro-benzoic acid methyl ester (8.20 g, 36.7 mmol, Step C) and 5,5-dibromobarbituric acid (7.35 g, 25.7 mmol) in 200 mL of THF was heated to reflux under N2 for 64 h. The solvents were removed, and the residue was partitioned between EtOAc and Na2CO3(aq). The organic portion was dried over MgSO4, filtered, condensed, and the titled compound was obtained as a white solid after flash column chromatography (5 to 20% of EtOAc in hexanes).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 64 h
  3. customThe solvents were removed
  4. customthe residue was partitioned between EtOAc and Na2CO3(aq)
  5. dry with materialThe organic portion was dried over MgSO4
  6. filtrationfiltered
  7. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-3016cb3c6a6a48d39e7b9ac70ffe8a63
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320992B2

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