Sodium Bromide → Methyl 2-(bromoacetyl)pent-2-enoate

HRID 992751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992751
[Br-:1].[Na+].[CH:3](=[C:6]([C:11]([CH2:13]Cl)=[O:12])[C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH3:5]>CN(C)C=O>[CH:3](=[C:6]([C:11]([CH2:13][Br:1])=[O:12])[C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH3:5]

Komponenten

4

Edukt 2

HCID 253881Sodium BromideHCID 53697886Methyl 2-propylidene-4-chloroacetoacetate

Produkt 1

HCID 54346073Methyl 2-(bromoacetyl)pent-2-enoateAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

In 10.23 g of N,N-dimethylformamide was dissolved 11.45 g of the concentrated solution (pure weight of methyl 2-propylidene-4-chloroacetoacetate: 4.57 g), and cooled to 10° C. To this mixture was added 6.17 g of sodium bromide, and thereafter heated to 22° C. and vigorously stirred at 22±2° C. for 2 hours. The resulting reaction solution was cooled to 5° C. and washed with 20 g of water, followed by being separated into an aqueous and organic layers. The high-performance liquid chromatography analysis of the organic layer indicated that this layer contained 4.66 g of methyl 2-propylidene-4-bromoacetoacetate (82.6% yield, E/Z ratio=52/48) and 9.7% of the starting material methyl 2-propylidene-4-chloroacetoacetate remained.

Aufarbeitung

  1. temperatureheated to 22° C.
  2. customThe resulting reaction solution
  3. temperaturewas cooled to 5° C.
  4. washwashed with 20 g of water
  5. customby being separated into an aqueous and organic layers

Quellen und Nachweise

ORD-Eintrag
ord-ec29e510e47742f1bcfefe11ae93cf09
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469200B1

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