Water → 2-Bromo-4-(2-fluorophenyl)thiazole

HRID 2263176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263176
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][S:10][C:11]#[N:12].[BrH:14].C(O)(=O)C.O>C(O)(=O)C>[Br:14][C:11]1[S:10][CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 18526224Thiocyanic acid, 2-(2-fluorophenyl)-2-oxoethyl esterHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 687812882-Bromo-4-(2-fluorophenyl)thiazoleAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 2-(2-fluorophenyl)-2-oxoethyl thiocyanate (4.20 g, 21.5 mmol) in acetic acid (40 ml) was added a solution of 25% hydrogen bromide/acetic acid (40 ml), and the mixture was stirred at 130° C. 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 purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (3.41 g, 61.4%) as an oil.

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 purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0dddba3fa67048e6a6b071751bd8556f
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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