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Sodium Hydroxide → 4-Carboxy-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole

HRID 434055
Notes
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Reaction equation

HRID 434055 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[I:19])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CCO>[C:4]([C:6]1[C:7]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[I:19])=[N:8][O:9][C:10]=1[CH3:11])([OH:5])=[O:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 227138064-Ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole

Product 1

HCID 179306454-Carboxy-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazoleYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole (7.15 g, 19 mmol) in EtOH (100 ml) was added 5N NaOH (7.6 ml, 38 mmol, 2 eq.), and stirred in a 50° C. oil bath for 4 hrs. The reaction was cooled to room temperature, poured into ice H2O and extracted with Et2O. The aqueous layer was then acidified to pH 3 using conc. HCl and extracted with ethyl acetate. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound (6.08 g, 92%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with Et2O
  3. extractionextracted with ethyl acetate
  4. washThe organic solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9458aec54dbc4005800f2cef312fa1c8
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06670373B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes