Lithium Hydroxide → 2-(2,6-Difluoro-4-methoxyphenyl)thiazole-4-carboxylic acid

HRID 521894Notes

Reaction equation

HRID 521894 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[S:12][CH:13]=[C:14]([C:16]([O:18]C)=[O:17])[N:15]=1.[OH-].[Li+]>CO.O>[F:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([F:1])[C:3]=1[C:11]1[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86713850Methyl 2-(2,6-difluoro-4-methoxy-phenyl)thiazole-4-carboxylate

Product 1

HCID 834100432-(2,6-Difluoro-4-methoxyphenyl)thiazole-4-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(2,6-difluoro-4-methoxy-phenyl)thiazole-4-carboxylate (2.403 mmol, 685.5 mg) in methanol (15 mL) and water (5 mL) was added lithium hydroxide (1.9 equiv., 4.54 mmol, 111 mg). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 1N HCl (aq.), then partitioned between EtOAc and brine. The organic layer was concentrated. The residue was dried on highvac to afford 2-(2,6-difluoro-4-methoxy-phenyl)thiazole-4-carboxylic acid (650 mg, quant.) as a brown solid.

Workup

  1. customThe reaction mixture was quenched with 1N HCl (aq.)
  2. custompartitioned between EtOAc and brine
  3. concentrationThe organic layer was concentrated
  4. customThe residue was dried on highvac

Sources & evidence

ORD record
ord-62921866205b4e1ba44c966182c57fa4
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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