Sodium Bicarbonate → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester

HRID 467939Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10](Cl)=[N:11][OH:12])=[CH:6][C:5]=1[C:14]([F:17])([F:16])[F:15].C(=O)([O-])O.[Na+].[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([C:33]([F:36])([F:35])[F:34])=[CH2:32])[CH:28]=[C:27]([Cl:37])[CH:26]=1>C(O)(C)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:32][C:31]([C:29]3[CH:28]=[C:27]([Cl:37])[CH:26]=[C:25]([Cl:24])[CH:30]=3)([C:33]([F:34])([F:36])[F:35])[O:12][N:11]=2)=[CH:6][C:5]=1[C:14]([F:17])([F:16])[F:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(chloro(hydroxyimino)methyl)-2-trifluoromethyl-benzoic acid methyl ester (Example I12) (4.21 g) in isopropanol (100 ml) was added sequentially sodium hydrogen carbonate (2.90 g) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (4.22 g) (prepared according to WO 2005/085216). The reaction mixture was stirred at 60° C. for 16 hours. The isopropanol was removed by distillation. The residue was purified over silica gel (eluent: ethyl acetate/heptane gradient from 0:1 to 2:3) to give 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoromethyl-benzoic acid methyl ester (4.30 g). 1H-NMR (CDCl3, 400 MHz): 8.00-7.44 (m, 6H), 4.12 (d, 1H), 3.96 (s, 3H), 3.74 (d, 1H).

Workup

customThe isopropanol was removed by distillation
customThe residue was purified over silica gel (eluent: ethyl acetate/heptane gradient from 0:1 to 2:3)

Sources & evidence

ORD record: ord-314b162631784cf7a54bd368638a3af1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623896B2

Reaction notes

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