반응 #1563929

반응 방정식

4-chloro-N-methoxy-N-methylbutanamide

2-Bromo-1,4-difluorobenzene

isopropyl magnesium chloride

→

title compound

수율 66.3%

4-chloro-1-(2,5-difluorophenyl)butan-1-one

수율 66.3%

용매

THF

THF

반응 조건

후처리

1. 1
   기타The reaction mixture thus obtained
2. 2
   온도The reaction mixture was cooled again to −50° C
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.WAITthe stirring was continued at 0° C. for 1 h
5. 5
   기타The reaction mixture was quenched with saturated aqueous NH4Cl solution
6. 6
   추출extracted with ethylacetate
7. 7
   기타The organic layer collected
8. 8
   세척was washed with water (500 mL)
9. 9
   건조with brine solution, dried over anhydrous sodium sulfate
10. 10
    농축concentrated under reduced pressure
11. 11
    기타to afford a crude liquid residue
12. 12
    기타The residue thus obtained
13. 13
    기타was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent)

실험 절차

2-Bromo-1,4-difluorobenzene (53.6 g, 277.74 mmol) in THF cooled to −50° C. was added to isopropyl magnesium chloride (2M in THF) (133 mL, 266 mmol). The reaction mixture thus obtained was warmed to 0° C. and stirred for 1 h. The reaction mixture was cooled again to −50° C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200 mL) was added dropwise to this reaction mixture with stirring and the stirring was continued at 0° C. for 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colourless liquid.

출처