![864736-32-3](/CAS/20200119/GIF/864736-32-3.gif)
4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester synthesis
- Product Name:4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester
- CAS Number:864736-32-3
- Molecular formula:C19H14Cl2F3NO3
- Molecular Weight:432.22
![1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene](/CAS/20150408/GIF/864725-22-4.gif)
864725-22-4
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![methyl 4-((hydroxyimino)methyl)-2-methylbenzoate](/CAS/20200331/GIF/1261169-50-9.gif)
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![4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester](/CAS/20200119/GIF/864736-32-3.gif)
864736-32-3
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Yield:864736-32-3 86.2 %
Reaction Conditions:
Stage #1: methyl 4-((hydroxyimino)methyl)-2-methylbenzoatewith N-chloro-succinimide in N,N-dimethyl-formamide at 40;
Stage #2: 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzenewith triethylamine in N,N-dimethyl-formamide;Cooling with ice;
Steps:
3.2.2. Synthesis of Intermediate C
Compound B (25.88 mmol), N-chlorosuccinimide (38.82 mmol), and DMF (30 mL) wereadded to a three-necked flask. The system was stirred at 40 C for 40 min, then cooled toroom temperature, and 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (31.06 mmol)and Et3N (38.82 mmol) were added under ice bath conditions. Monitoring of reactioncompletion by TLC, ethyl acetate was added to the crude products and then extracted, andthe organic layer was collected. Intermediate C was obtained after purification by columnchromatography (petroleum ether: ethyl acetate = 5:1 (v/v)).
References:
Li, Fangyi;Jiang, Biaobiao;Luo, Yuqin;He, Siqi;Feng, Di;Hu, Deyu;Song, Runjiang [Molecules,2023,vol. 28,# 8,art. no. 3300] Location in patent:supporting information
![Methyl 4-forMyl-2-Methylbenzoate](/CAS/GIF/74733-23-6.gif)
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![4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester](/CAS/20200119/GIF/864736-32-3.gif)
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![4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester](/CAS/20200119/GIF/864736-32-3.gif)
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![4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester](/CAS/20200119/GIF/864736-32-3.gif)
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