Lithium Hydroxide → 2-Bromo-1,3-thiazole-4-carboxylic acid

HRID 1990991Notes

Reaction equation

HRID 1990991 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:11])[S:9][CH:10]=1)=[O:5])C.[Li+].[OH-]>CO.O>[Br:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

Product 1

HCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2-bromo-thiazole-4-carboxylic acid ethyl ester (Combi-Blocks, Inc., San Diego, Calif.; 5 g, 21.2 mmol) in MeOH (25 mL) and water (25 mL) was added LiOH (0.56 g, 23.3 mmol). After stirring for 4 h at reflux temperature, MeOH was evaporated in vacuo. To the residue was added more water, the mixture was acidified to pH 2 with concentrated HCl (3 mL), and extracted with EtOAc. The combined extracts were evaporated to give 2-bromo-thiazole-4-carboxylic acid which was used without further purification. The compounds of the present invention were preferably prepared by methods A to F:

Workup

  1. customwas evaporated in vacuo
  2. additionTo the residue was added more water
  3. extractionextracted with EtOAc
  4. customThe combined extracts were evaporated

Sources & evidence

ORD record
ord-f18a04ff8fc541c197f0d420b87b9063
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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