反应 #595298

反应方程式

2′,4′-difluoroacetophenone

diethyl 2-chlorobenzylphosphonate

sodium hydride

→

1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene

收率 26.0%

溶剂

DMF

water

DMF

反应条件

后处理

1. 1
   洗涤freshly washed with dry heptane) in dry DMF (20 ml)
2. 2
   workup.STIRRINGThe resulting mixture was stirred at RT for 68 h
3. 3
   萃取extracted with diethyl ether
4. 4
   其他The organic phase was dried
5. 5
   浓缩concentrated to dryness under reduced pressure
6. 6
   其他the residue was purified by chromatography on silica gel, which

实验过程

At 3° C., a solution of diethyl 2-chlorobenzylphosphonate (2.00 g, 7.61 mmol) in dry DMF (30 ml) was added to a stirred suspension of sodium hydride (60% by weight suspension in mineral oil, 365 mg, 9.13 mmol; freshly washed with dry heptane) in dry DMF (20 ml). After 1 h of stirring at 3° C., a solution of 2′,4′-difluoroacetophenone (1.31 g, 8.37 mmol) in dry DMF (20 ml) was added dropwise. The resulting mixture was stirred at RT for 68 h and then diluted with water and extracted with diethyl ether. The organic phase was dried and concentrated to dryness under reduced pressure, and the residue was purified by chromatography on silica gel, which gave 1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene as a 93/7 mixture of diastereoisomers [colourless solid, 560 mg, yield 26%; GC/MS: m/z=264 (M+); HPLC/MS: log P(HCOOH)=5.05 (major diastereoisomer), 5.34 (minor diastereoisomer)].

来源