Methanol → 2-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzoic Acid Methyl Ester

HRID 1022836Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[Cl:25].[C:26]([O-:29])(=[O:28])C.[Na+].[C]=O.[CH3:33]O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:33][O:29][C:26](=[O:28])[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:14])([F:15])[F:16])[O:10][N:9]=2)=[CH:4][C:3]=1[Cl:25]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(4-bromo-3-chloro-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (4.00 g), palladium bis(diphenylphosphine) dichloride CH2Cl2-complex (0.69 g), palladium acetate (0.14 g), sodium acetate (1.03 g), and methanol (50 mL) was placed in an autoclave, charged with 5 bar of carbon monoxide and stirred at 100° C. for 16 h. After cooling, the autoclave was opened and the reaction mixture was filtered. The filtrate was concentrated in vacuum and the residue was purified by flash chromatography on silica gel to obtain the title compound (2.2 g, 58%).

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
concentrationThe filtrate was concentrated in vacuum
customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-d53663fd48c14148adbd6408196f5709
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722673B2

Reaction notes

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