Reacción #1951069

Ecuación de reacción

4-Fluorophenyl-phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

4-fluoro-phenyl-divinyl-phosphine oxide

Rendimiento 83.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   ExtracciónThe product was extracted into dichloromethane
4. 4
   Lavadowashed with saturated aqueous sodium bicarbonate
5. 5
   SecadoThe organic phase was dried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated by rotary evaporation

Procedimiento

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.

Fuente