Hydrochloric Acid → 5-Bromo-4-methylisoxazole-3-carboxylic acid
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated under reduced pressure
- customto remove MeOH
- additionThe aqueous was diluted with water
- extractionextracted with EtOAc (×3)
- dry with materialthe combined organic extracts were dried over MgSO4
- filtrationfiltered
- 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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