Water → HCID 58262208, compound

Participants

Reaction Steps

Diethyl 3,4,5-trifluorobenzylphosphonate (2.80 g, 9.92 mmol) was dissolved in dry dichloromethane (30 mL). Bromotrimethylsilane (4.1 mL, 31.7 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 large white needles (2.00 g, 89% yield). 1H NMR (400.14 MHz, DMSO) δ 7.16 (m, 2H), 2.99 (d, J=21.4 Hz, 2H). 13C {1H} NMR (100.62 MHz, DMSO) δ 149.9 (dddd, J=246, 9.6, 3.6, 3.6 Hz, 2C), 137.5 (dtd, J=247, 15.4, 3.7), 132.1-131.8 (m), 114.4-114.1 (m, 2C), 34.42 (d, J=132 Hz). 31P {1H} NMR (161.97 MHz, DMSO): δ 20.54. Analysis calculated (found) %: C 37.19 (37.17), H 2.67 (2.63). MS (FAB, m/z): 227 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 227.00849 (227.00670).

Provenance & Evidence