反应 #1951067

反应方程式

4-Bromo-fluorobenzene

diethyl phosphite

triethylamine

→

4-fluorophenyl-phosphonic acid diethyl ester

收率 94.0%

溶剂

ethyl acetate

反应条件

后处理

1. 1
   其他The resulting solution was degassed with nitrogen
2. 2
   温度to cool to ambient temperature
3. 3
   洗涤The solution was washed with saturated sodium bicarbonate (350 mL)
4. 4
   workup.DISTILLATIONThe crude product was purified by vacuum distillation (ca. 98° C., 0.6 Torr)

实验过程

4-Bromo-fluorobenzene (10.95 g, 62.57 mmol) was added to diethyl phosphite (8.86 mL, 68.8 mmol) at ambient temperature, followed by the addition of triethylamine (9.6 mL, 68.8 mmol). The resulting solution was degassed with nitrogen followed by the addition of tetrakis(triphenylphosphine)-palladium (3.0 g, 2.6 mmol). The resulting mixture was heated at 90° C. overnight. The reaction mixture was allowed to cool to ambient temperature and then ethyl acetate (350 mL) was added. The solution was washed with saturated sodium bicarbonate (350 mL) and then with saturated brine (2×350 mL). The crude product was purified by vacuum distillation (ca. 98° C., 0.6 Torr) to yield 8.956 g of 4-fluorophenyl-phosphonic acid diethyl ester (38.6 mmol, 94% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.88-7.80 (m, 2H); 7.20-7.14 (m 2H); 4.22-4.04 (m, 4H); 1.36-1.32 (t, 6H); ESMS (m/z): M+1)+ found, 233.

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