Methanol → 4-Carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole

HRID 434050Notes

Reaction equation

HRID 434050 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].CO>C1COCC1>[C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18756263Ethyl 3-(4-bromo-2-fluorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 187562854-Carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazoleYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a fashion similar to that described for preparation 16 (120 mg), 4-ethoxycarbonyl-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole (350 mg, 1.06 mmol), 5N NaOH (1 ml, 5 mmol), methanol (5 ml), and THF (1 ml) gave 4-carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole (320 mg, 100%) that was used without purification.

Sources & evidence

ORD record
ord-23a7f48b2f134449bd58e0bdc466625e
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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