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

HRID 471379Notes

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-1cd2dcdcab14473d9006c4c3120ded86
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633134B2

Reaction notes

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