Diazomethane → 5-Bromo-1-diazo-3-(3,4-dichlorophenyl)-2-pentanone

HRID 1939840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1939840
[N+:1](=[CH2:3])=[N-:2].CN(N=O)/C(/N)=N/[N+]([O-])=O.[OH-].[K+].[Br:16][CH2:17][CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[C:20](Cl)=[O:21]>CCOCC>[Br:16][CH2:17][CH2:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[C:20](=[O:21])[CH:3]=[N+:1]=[N-:2]

Komponenten

6

Edukt 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 95620601-Methyl-2-nitro-1-nitrosoguanidineHCID 54519315alpha-(2-Bromoethyl)-3,4-dichlorophenylacetic acid chloride

Produkt 1

HCID 537812765-Bromo-1-diazo-3-(3,4-dichlorophenyl)-2-pentanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Prepare a solution of diazomethane from 15 g of MNNG by reaction with 45 ml of 40% aqueous KOH topped with 150 ml. of Et2O and cool in an ice bath. Add an Et2O solution (40 ml.) of the product of Step 3 (8.2 g, 24.8 mmoles) in small volumes, stir the solution in the ice bath for 15 min, then heat to reflux for 30 min. Remove the solvent in vacuo. Purify the resulting mixture by flash chromatography on silica gel using CH2Cl2 as eluent. Yield: 7.0 g (IR: 2100 cm-1, 1630 cm-1).

Aufarbeitung

  1. temperatureheat
  2. temperatureto reflux for 30 min
  3. customRemove the solvent in vacuo
  4. customPurify the resulting mixture by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ae97e286e911405e844d7818b1508d61
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696267

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