Hydrochloric Acid → 5-Bromo-4-methylisoxazole-3-carboxylic acid

HRID 1478178Notes

Reaction equation

HRID 1478178 reaction equation
[Br:1][C:2]1[O:6][N:5]=[C:4]([C:7]([O:9]CC)=[O:8])[C:3]=1[CH3:12].[OH-].[Na+].Cl>CO>[Br:1][C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=[O:8])[C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2×

Product 1

HCID 231371575-Bromo-4-methylisoxazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (8.65 g, 37.0 mmol) in MeOH (100 mL) was added 2M NaOH (aq) (18.48 mL, 37.0 mmol). The reaction mixture was stirred at room temperature for 10 minutes and the resulting mixture was acidified using 1M HCl (aq) and concentrated under reduced pressure to remove MeOH. The aqueous was diluted with water and extracted with EtOAc (×3) and the combined organic extracts were dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound;

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove MeOH
  3. additionThe aqueous was diluted with water
  4. extractionextracted with EtOAc (×3)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-47e80a5d81c64b92aa590521fc9b8f9a
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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