반응 #1951058

반응 방정식

4-Fluorobenzyl phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

(4-fluorophenylmethyl) divinyl phosphine oxide

수율 84.0%

반응 조건

후처리

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   추출The product was extracted into dichloromethane
4. 4
   세척washed with saturated aqueous sodium bicarbonate
5. 5
   건조The organic phase was dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated by rotary evaporation

실험 절차

4-Fluorobenzyl phosphonic dichloride (1.71 g, 7.82 mmol) was dissolved in 10 mL of dry THF, under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise vinyl magnesium bromide in THF (18.3 mL, IM). The resulting solution was stirred for 30 minutes at −70° C. An aqueous solution of ammonium chloride (100 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, and then with water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 1.375 g of (4-fluorophenylmethyl) divinyl phosphine oxide (6.55 mmol, 84%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.20-7.14 (m, 2H); 7.01-6.95 (m 2H); 6.29-6.08 (m, 6H); 3.20-3.15 (d, 2H); ESMS (m/z): (M+1)+found, 211.

출처