Hydrogen Bromide → 4-Bromo-3,5-dichloro-benzoic acid methyl ester

HRID 1441042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441042
N[C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:13].N([O-])=O.[Na+].[BrH:18]>>[Br:18][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:13]

Komponenten

4

Edukt 3

HCID 260Hydrogen Bromide2×HCID 604808Methyl 4-amino-3,5-dichlorobenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 508496864-Bromo-3,5-dichloro-benzoic acid methyl ester

Versuchsvorschrift

Methyl 4-amino-3,5-dichlorobenzoate (32 g.) dissolved in 48% hydrobromic acid (100 ml.) was cooled to 0° and sodium nitrite (10.5 g.) was added. The solution was added slowly to a mixture of 48% hydrobromic acid (80 ml.) and cuprous bromide (35 g.) and the mixture heated at reflux for 2 hours. After cooling, the mixture was extracted with ethyl acetate and the organic extracts washed with brine, dried (anhydrous magnesium sulphate) and evaporated to give a dark solid. Crystallisation from ethyl acetate gave methyl 4-bromo-3,5-dichlorobenzoate (20 g.). Nuclear Magnetic Resonance Spectrum (NMR) was as follows: 1H: 4.0,3H,s; 7.9,2H,s.

Aufarbeitung

  1. temperaturewas cooled to 0°
  2. temperaturethe mixture heated
  3. temperatureat reflux for 2 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe organic extracts washed with brine
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. customevaporated
  9. customto give a dark solid
  10. customCrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4c50af6bdc694b3ca484f8f44726caad
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05502073

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