Dimethyl Sulfoxide → 3-(2-Bromo-6-nitrophenyl)-2-propenenitrile

HRID 1005668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005668
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=O.[O-2].[Mg+2].CS(C)=O.[C:19]([CH2:21]P(=O)(OCC)OCC)#[N:20]>C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=[CH:21][C:19]#[N:20]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 6850729Magnesium monoxideHCID 150631742-Bromo-6-nitrobenzaldehyde

Produkt 1

HCID 684976623-(2-Bromo-6-nitrophenyl)-2-propenenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After stirring 2-bromo-6-nitrobenzaldehyde (30.4 g), magnesium oxide (75 g) and dimethyl sulfoxide (11.3 ml) sufficiently for 1 minute, diethyl (cyanomethyl)phosphonate (25.8 ml) was added thereto and the mixture was stirred for further 2 hours. After the completion of stirring, the mixture was left stand overnight. Then, ethyl acetate was added thereto, and the mixture was stirred and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate), to give 32 g of 3-(2-bromo-6-nitrophenyl)-2-propenenitrile (E-isomer:Z-isomer=3:1).

Aufarbeitung

  1. stirringAfter the completion of stirring
  2. waitthe mixture was left stand overnight
  3. stirringthe mixture was stirred
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ec68f06b9c7c4b0394e797bffca3aad2
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787534B2

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