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

HRID 1173113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173113
[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(OC(=O)C)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

2-Bromo-6-nitrobenzaldehyde (30.4 g), magnesium oxide (75 g) and dimethyl sulfoxide (11.3 ml) were sufficiently stirred for one minute. Then, to the mixture was added diethyl (cyanomethyl)phosphonate (25.8 ml) and the mixture was stirred for further 2 hours. The stirring was stopped and the reaction mixture was allowed to stand overnight. Thereafter, ethylacetate was added thereto and the resulting mixture was stirred, followed by filtering. 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. waitto stand overnight
  2. stirringthe resulting mixture was stirred
  3. filtrationby filtering
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-846cdc69738f4ee084959a17b37225ce
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834049B2

Notizen zur Reaktion

Wird geladen…