تفاعل #1951058

معادلة التفاعل

4-Fluorobenzyl phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

(4-fluorophenylmethyl) divinyl phosphine oxide

المردود 84.0%

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   استخلاصThe product was extracted into dichloromethane
4. 4
   غسيلwashed with saturated aqueous sodium bicarbonate
5. 5
   تجفيفThe organic phase was dried with sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated by rotary evaporation

الإجراء التجريبي

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.

المصدر