Water → 2,6-Difluorobenzylphosphonic acid

Participants

Reaction Steps

Diethyl 2,6-difluorobenzylphosphonate (2.00 g, 7.57 mmol) was dissolved in dry dichloromethane (20 mL). Bromotrimethylsilane (3.3 mL, 25 mmol) was added via syringe. The reaction was capped with a greased glass stopper and allowed to stir for 6 hours. The volatiles were removed under reduced pressure to yield a yellow oil. This was dissolved in 10:1 methanol:water (20 mL) and allowed to stir overnight. After removing the solvents, recrystallization in acetonitrile yielded a white crystalline solid (1.199 g, 76% yield). 1H NMR (400.14 MHz, DMSO) δ 7.29 (m), 7.04 (m, 2H), 2.96 (d, J=20.99 Hz, 2H). 31P {1H} NMR (161.97 MHz, DMSO): δ 19.51. Analysis calculated (found) %: C 40.40 (40.64), H 3.39 (3.34).

Provenance & Evidence