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

HRID 521920Notes

Reaction equation

HRID 521920 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-31c0f49ce8b14ad8ad4f63216388c981
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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