Water → 4-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

HRID 1848315Notes

Reaction equation

C[N:2](C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]([C:28]([F:31])([F:30])[F:29])=[CH:15][C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[C:20]([CH3:27])[CH:19]=2)=O)[CH:10]=[C:11]([Cl:13])[CH:12]=1.C1(C)C=CC=CC=1.[OH2:39]>[OH-].[Na+].S(O)(O)(=O)=O.NO>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:28]([F:31])([F:30])[F:29])[O:39][N:2]=[C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[C:20]([CH3:27])[CH:19]=3)[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.2 g of dimethylformamide was added to solution in which 1.61 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid was dissolved into 8.51 g of toluene, and the mixture was cooled to 0° C. A solution in which 0.64 g of sodium hydroxide was dissolved into 1.6 g of water was added to the mixture, and a solution in which 0.46 g of hydroxylamine sulfate dissolved into 1.11 g of water was slowly added in dropwise with care not to generate heat. After reacting the mixture for 3 hours with stirring while keeping the reaction temperature at 0° C., the resultant solution was analyzed by high-performance liquid chromatography (wavelength 254 nm). The target product of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid was produced in 90.49% of relative area.

Workup

additionwas added to the mixture
additionwas slowly added in dropwise with care not
temperatureto generate heat
customfor 3 hours
customat 0° C.

Sources & evidence

ORD record: ord-c7d150fe724a48cfb27067762dcc5941
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

Loading…