Hydrochloric Acid → 2-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-cyclopropanecarboxylic acid

HRID 1183309Notes

Reaction equation

HRID 1183309 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[C:10]([CH3:21])=[N:11][O:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)=[O:5])C.CO.[OH-].[Na+].Cl>C1COCC1>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[O:12][N:11]=[C:10]([CH3:21])[C:9]=2[CH:7]2[CH2:8][CH:6]2[C:4]([OH:5])=[O:3])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 665776142-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 665776812-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-cyclopropanecarboxylic acid ethyl ester (more polar isomer, 0.164 g, 0.468 mmol) was dissolved in THF (3 mL) then MeOH (1 mL) and NaOH (1N aq., 1 mL) were added. The reaction stirred at room temperature overnight and was then acidified with 1N aq. HCl and submitted to standard aqueous workup to afford the title compound.

Sources & evidence

ORD record
ord-5e29bff538bf44aca1114ad13fda0277
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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