반응 #87222

반응 방정식

N-chlorosuccinimide

1,3-difluoro-2-((2-methylallyloxy)methyl)benzene

NaHCO3

2-fluorobenzaldehyde oxime

→

5-((2,6-difluorobenzyloxy)methyl)-3-(2-fluorophenyl)-5-methyl-4,5-dihydroisoxazole

수율 79.9%

용매

dimethylformamide

dichloromethane

1,2-dichloroethane

반응 조건

후처리

1. 1
   기타at a temperature of 0° C
2. 2
   온도the reaction mixture was cooled to a temperature 0° C.
3. 3
   workup.ADDITIONslowly added
4. 4
   workup.STIRRINGThe reaction mixture was stirred at room temperature overnight
5. 5
   세척washed with water
6. 6
   기타the obtained organic layer was dried
7. 7
   농축concentrated
8. 8
   기타the concentrate was separated by silicagel column chromatography

실험 절차

200 mg of 2-fluorobenzaldehyde oxime was dissolved in 4 mL of 1,2-dichloroethane, and then, 230 mg of N-chlorosuccinimide and 0.4 mL of dimethylformamide were slowly added thereto at a temperature of 0° C. The reaction mixture was stirred at room temperature for 1 hour, and then, the reaction state was confirmed by TLC. When the oxime, which was a starting material, disappeared, the reaction mixture was cooled to a temperature 0° C., and then, 182 mg of NaHCO3, 27 mg of tetrabutylammonium iodide, and 342 mg of 1,3-difluoro-2-((2-methylallyloxy)methyl)benzene were sequentially, slowly added thereto. The reaction mixture was stirred at room temperature overnight, and then, diluted with dichloromethane, and then, washed with water, and the obtained organic layer was dried by using magnesium sulfate and concentrated, and the concentrate was separated by silicagel column chromatography to obtain 385 mg of 5-((2,6-difluorobenzyloxy)methyl)-3-(2-fluorophenyl)-5-methyl-4,5-dihydroisoxazole.

출처