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

HRID 872708Notes

Reaction equation

HRID 872708 reaction equation
[Br:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9]CC)=[O:8])[N:6]=1.[OH-].[Li+]>C1COCC1.CO.O>[Br:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 26370035Ethyl 2-bromo-1,3-oxazole-4-carboxylate

Product 1

HCID 533995362-Bromo-1,3-oxazole-4-carboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 2-bromo-1,3-oxazole-4-carboxylate (2.5 g, 11.36 mmo) was dissolved in THF/methanol mixture (9:1) and 1M lithium hydroxide (22.73 ml, 22.73 mmol) was added slowly. The reaction mixture was stirred at RT for 1 h, diluted with water and pH was adjusted to 2. Formed precipitate was filtered and dried to yield the title compound (1.1 g). The filtrate was extracted three times with ethyl acetate. Ethyl acetate phases were combined, dried and evaporated to dryness to yield the title compound 0.85 g. Total yield 88%. m/z [192.0+1]

Workup

  1. customFormed precipitate
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-9e4626c765a940a78beff153896bfcd0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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