Trimethyl phosphite → HCID 23208053, compound

Temperature

110 °C

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.

1. customat 90° C.
2. customovernight
3. temperatureto cool to ambient temperature
4. washThe solution was washed with saturated sodium bicarbonate (350 mL)
5. dry with materialThe organic phase was dried with magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated by rotatry evaporation
8. customThe resulting crude product was purified by flash silica chromatrography

ORD record

ord-8cabd193a6274e308e46071ebbde90ad

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625880B2