Reaktion #78797

ord-001383a7dc4048e8b945bdebc5387987

Reaktionsgleichung

O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1
2,4-dinitrophenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
BrCC=CCBr
1,4-dibromo-2-butene
→
O=[N+]([O-])c1ccc(OCC=CCBr)c([N+](=O)[O-])c1
1-bromo-4-(2,4-dinitrophenyloxy)but-2-ene
Ausbeute 46.7%

Edukte

O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1
2,4-dinitrophenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
BrCC=CCBr
1,4-dibromo-2-butene

Reagenzien

Keine

Lösungsmittel

CN1CCCC1=O
NMP

Reaktionsbedingungen

Temperatur
45°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionExtraction
  2. 2
    workup.DISTILLATIONin the normal fashion and Kugelrohr distillation of the excess dibromide (0.1 mm Hg, 80° C.)

Vorschrift

A mixture of 2,4-dinitrophenol (4.6 g, 80 wt %), potassium carbonate (4.2 g), NMP (40 mL) and 1,4-dibromo-2-butene (12.8 g) was heated to 45° C. for 2 hr. Extraction in the normal fashion and Kugelrohr distillation of the excess dibromide (0.1 mm Hg, 80° C.) gave 1-bromo-4-(2,4-dinitrophenyloxy)but-2-ene (3.7 g, mp 55-57° C.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713135B2uspto-grants-2004_03