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Hydrochloric Acid → Tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoate

HRID 69111
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69111
[Cl-].[Mg+2].[Cl-].[O:4]=[C:5]([CH3:14])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1.Cl>O1CCCC1.C(OCC)(=O)C.O.N1C=CC=CC=1>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([CH:6]([C:5](=[O:4])[CH3:14])[C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])=[O:21])=[C:18]([N+:25]([O-:27])=[O:26])[CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 15538Tert-butyl acetoacetateHCID 5360315Magnesium ChlorideHCID 189198804-Bromo-2-nitrobenzoyl chloride

Produkt 1

HCID 86694315Tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3-oxobutanoateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962
Water
Lösungsmittel
HCID 1049PyridineLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-8 °C

Versuchsvorschrift

Under a nitrogen atmosphere, to a suspension of 2.28 g of magnesium chloride in 50 mL of tetrahydrofuran was added 3.80 g of tert-butyl 3-oxobutanoate at room temperature. The mixture was cooled to −8° C., and 3.9 mL of pyridine was added thereto, followed by stirring at the same temperature for 30 minutes, warming to room temperature, and further stirring for 30 minutes. The mixture was cooled to −8° C., and a solution of 5.3 g of 4-bromo-2-nitrobenzoyl chloride in 20 mL of tetrahydrofuran was added thereto, followed by stirring at the same temperature for 1 hour, warming to room temperature, and further stirring for 1.5 hours. The mixture was poured into a mixture of water and ethyl acetate, and adjusted to pH 3 with concentrated hydrochloric acid. The aqueous layer was separated, and then the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4.95 g of tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3 -oxobutanoate.

Aufarbeitung

  1. temperaturewarming to room temperature
  2. stirringfurther stirring for 30 minutes
  3. temperatureThe mixture was cooled to −8° C.
  4. stirringby stirring at the same temperature for 1 hour
  5. temperaturewarming to room temperature
  6. stirringfurther stirring for 1.5 hours
  7. customThe aqueous layer was separated
  8. washthe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2785f0f145504683ba851c929693a5f8
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822448B2

Notizen zur Reaktion

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