Water → Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate

HRID 1169353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169353
[O-]CC.[Na+].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16].O>C(O)C.C1(C)C=CC=CC=1>[N:14](/[C:17](=[CH:10]\[C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[CH:7][CH:8]=1)/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]

Komponenten

7

Edukt 4

HCID 962WaterHCID 69480Acetic acid, azido-, ethyl esterHCID 707414-BromobenzaldehydeHCID 2723922Sodium ethoxide

Produkt 1

HCID 24767341Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Into a solution of sodium ethoxide (a 20% solution in ethanol, 22.2 g) in toluene (100 ml) was added at 0° C. over a period of more than 10 minutes a solution of 4-bromobenzaldehyde (10 g) and ethyl azidoacetate (7.0 g) in toluene (50 ml). After being stirred at room temperature for 2 hours, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:19) to obtain ethyl (Z)-2-azido-3-(4-bromophenyl)acrylate (6.24 g) as a yellow oily substance.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialwas dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to separation and purification

Quellen und Nachweise

ORD-Eintrag
ord-b5f4680863cc4c45a60cd640bde76739
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627651B1

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