反应 #1951056

反应方程式

4-fluorobenzyl bromide

trimethyl phosphite

→

(4-fluoro-benzyl)-phosphonic acid dimethyl ester

收率 67.5%

溶剂

ethyl acetate

反应条件

后处理

1. 1
   其他at 90° C.
2. 2
   其他overnight
3. 3
   温度to cool to ambient temperature
4. 4
   洗涤The solution was washed with saturated sodium bicarbonate (350 mL)
5. 5
   干燥The organic phase was dried with magnesium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated by rotatry evaporation
8. 8
   其他The resulting crude product was purified by flash silica chromatrography

实验过程

4-fluorobenzyl bromide (25 mL, 0.20 mol) was added to a stirred solution of trimethyl phosphite (35.9 mL, 0.30 mol) at ambient temperature, under a nitrogen atmosphere. The resulting solution was heated at 110° C. for six hours, and then 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 organic phase was dried with magnesium sulfate, filtered, and concentrated by rotatry evaporation. The resulting crude product was purified by flash silica chromatrography using 0-35% acetonitrile in ethyl acetate as eluant to yield (4-fluoro-benzyl)-phosphonic acid dimethyl ester (29.44 g, 135 mmol, 66% yield) as a colorless oil. 1H NMR (400 MHz, DMSO) δ 7.33-7.28 (m, 2H); 7.17-7.12 (dd, 2H); 3.61-3.58 (d, 6H); 3.31-3.24 (d, 2H); ESMS (m/z): (M+1)+ found, 219.

来源