StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Isobutyric Acid → Ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1051304
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1051304
C(=O)([O-])O.[K+].Br[C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1.[CH3:17][C:18]1[N:19]=[CH:20][S:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(O)(=O)C(C)C.C(P(C(C)(C)C)C1CCCCC1)(C)(C)C>C1(C)C=CC=CC=1.Cl[Pd]Cl.[Cu](Br)Br>[F:16][C:10]1[CH:9]=[CH:8][C:7]([C:20]2[S:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]([CH3:17])[N:19]=2)=[CH:12][C:11]=1[N+:13]([O-:15])=[O:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6590Isobutyric AcidHCID 2986105-Thiazolecarboxylic acid, 4-methyl-, ethyl esterHCID 516893Potassium BicarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 4643321Di-tert-butylcyclohexylphosphine

Produkt 1

HCID 118555037
Ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate
Ausbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24290Palladium ChlorideKatalysatorHCID 24611Copper bromide (CuBr2)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture was prepared by adding 2.10 g of potassium hydrogen carbonate, 44 mg of palladium chloride (II) and 205 mg of a copper bromide (I) dimethylsulfide complex to 2.20 g of 5-bromo-2-fluoronitrobenzene and the resulting mixture was suspended in 20 mL of toluene. Subsequently, a reaction mixture solution prepared by adding 2.05 g of ethyl 4-methyl-1,3-thiazole-5-carboxylate, 92.5 μL of isobutyric acid and 228 mg of di-t-butylcyclohexylphosphine to the resulting suspension was heated at 120° C. for 14 hours under a nitrogen atmosphere. The reaction mixture solution was celite-filtered to remove insoluble matter and water was added to the filtrate, and extraction was performed using ethyl acetate. The organic layer was washed with saline and dried and concentrated under reduced pressure. The resulting crude product was separated and purified by silica gel column chromatography to obtain 2.28 g of ethyl 2-(4-fluoro-3-nitrophenyl)-4-methyl-1,3-thiazole-5-carboxylate.

Aufarbeitung

  1. customA mixture was prepared
  2. customSubsequently, a reaction mixture solution prepared
  3. filtrationThe reaction mixture solution was celite-filtered
  4. customto remove insoluble matter and water
  5. additionwas added to the filtrate, and extraction
  6. washThe organic layer was washed with saline
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude product was separated
  10. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d31b808f8970403682c7aaac07b92084
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388174B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion