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Hydrogen Bromide → 2-Bromo-4-(trifluoromethyl)-1,3-thiazole

HRID 1670748
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1670748
N[C:2]1[S:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[BrH:11].N([O-])=O.[Na+].S([O-])(O)=O.[Na+].[OH-].[Na+]>O>[Br:11][C:2]1[S:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Produkt 1

HCID 231498872-Bromo-4-(trifluoromethyl)-1,3-thiazoleAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Amino-4-(trifluoromethyl)thiazole (Wako Pure Chemical Industries, Ltd., 500 mg) was added to 48% aqueous hydrogen bromide (6 ml) and, under ice-cooling, sodium nitrite (266 mg) dissolved in water (1 ml) was added dropwise thereto. The mixture was stirred at 0° C. for 1 hr. A sodium hydrogen sulfite aqueous solution, and then an aqueous sodium hydroxide solution were added, and the mixture was extracted with diethyl ether. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-hexane (1:9)) to give 2-bromo-4-(trifluoromethyl)thiazole (167 mg, yield 24%).

Aufarbeitung

  1. temperaturecooling
  2. additionwas added dropwise
  3. extractionthe mixture was extracted with diethyl ether
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-hexane (1:9))

Quellen und Nachweise

ORD-Eintrag
ord-a61a544eec764607878ecb9d6acd7b3d
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07994196B2

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