Water → 2-Bromo-4-(4-fluorophenyl)-1,3-thiazole

HRID 2263185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263185
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])=[CH:4][CH:3]=1.[BrH:14].C(O)(=O)C.O>C(O)(=O)C>[Br:14][C:11]1[S:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 41989922-(4-Fluorophenyl)-2-oxoethyl thiocyanateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 389962072-Bromo-4-(4-fluorophenyl)-1,3-thiazoleAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 2-(4-fluorophenyl)-2-oxoethyl thiocyanate (3.70 g, 19.0 mmol) in acetic acid (35 ml) was added a 25% hydrogen bromide/acetic acid (35 ml) solution, and the mixture was stirred at 130° C. for 2 hours and at room temperature for 2 hours. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethanol and water to give the desired product (4.50 g, 91.9%) as a solid.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of ethanol and water

Quellen und Nachweise

ORD-Eintrag
ord-301c5a66f5944c4cba5c25fb69182320
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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