反応 #1563929

反応方程式

4-chloro-N-methoxy-N-methylbutanamide

2-Bromo-1,4-difluorobenzene

isopropyl magnesium chloride

→

title compound

収率 66.3%

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

収率 66.3%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The reaction mixture thus obtained
2. 2
   温度The 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
   その他The reaction mixture was quenched with saturated aqueous NH4Cl solution
6. 6
   抽出extracted with ethylacetate
7. 7
   その他The organic layer collected
8. 8
   洗浄was washed with water (500 mL)
9. 9
   乾燥with brine solution, dried over anhydrous sodium sulfate
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他to afford a crude liquid residue
12. 12
    その他The residue thus obtained
13. 13
    その他was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent)

実験手順

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.

出典