反应 #1951069

反应方程式

4-Fluorophenyl-phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

4-fluoro-phenyl-divinyl-phosphine oxide

收率 83.0%

反应条件

后处理

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   萃取The product was extracted into dichloromethane
4. 4
   洗涤washed with saturated aqueous sodium bicarbonate
5. 5
   干燥The organic phase was dried with sodium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated by rotary evaporation

实验过程

4-Fluorophenyl-phosphonic dichloride (6.86 g, 32.2 mmol) was dissolved in dry THF (50 mL), placed under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise a solution of vinyl magnesium bromide in THF (80.5 mL, 1 M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2 M) was chilled to 0° C. and stirred rapidly while the cold reaction mixture was added. The product was extracted into dichloromethane and washed with saturated aqueous sodium bicarbonate followed by water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 5.214 g of 4-fluoro-phenyl-divinyl-phosphine oxide (26.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.80-7.71 (m, 2H); 7.25-7.18 (m 2H); 6.56-6.22 (m, 6H); ESMS (m/z): (M+1)+ found, 197.

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