Lithium Hydroxide → 2-(5-Bromo-2-fluorophenyl)-1,3-thiazole-4-carboxylic acid

HRID 521920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521920
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=2)[CH:7]=1.[OH-].[Li+]>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=2)[CH:7]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86713863Ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate

Produkt 1

HCID 826480922-(5-Bromo-2-fluorophenyl)-1,3-thiazole-4-carboxylic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate (8.97 mmol, 2960 mg) in methanol (40 mL) and water (10 mL) was added lithium hydroxide (1.6 equiv., 14.2 mmol, 347 mg). The reaction mixture was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated, suspended in water, and then quenched with 2N HCl(aq.). The solid was collected, washed with water, and dried under high vacuum to afford 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylic acid (2410 mg, 89% Yield) as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customquenched with 2N HCl(aq.)
  4. customThe solid was collected
  5. washwashed with water
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-31c0f49ce8b14ad8ad4f63216388c981
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328106B2

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