Hydrochloric Acid → 3-Bromoisoxazole-5-carboxylic acid

HRID 2233886Notes

Reaction equation

HRID 2233886 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[O:4][N:3]=1.[OH-].[Na+].Cl>CO.O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13802099Ethyl 3-bromo-1,2-oxazole-5-carboxylate2×

Product 1

HCID 3277163-Bromoisoxazole-5-carboxylic acidYield 80.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 442 mg (2.0 mmol) of ethyl 3-bromoisoxazole-5-carboxylate (Intermediate 119) and 5.0 ml of 1 N sodium hydroxide in 10 ml of MeOH was stirred at ambient temperature for 5 h, then acidified with 6.0 ml of 1 N hydrochloric acid, diluted with 25 ml of water and extracted with EtOAc (3×25 ml). The combined organic extract was dried over magnesium sulfate and concentrated in vacuo to give the title compound as a white solid (310 mg).

Workup

  1. extractionextracted with EtOAc (3×25 ml)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e95547fe73ec49afb5762152ccf18e66
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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