Water → HCID 67078811, compound

Participants

Reaction Steps

Diethyl 12-(1,3-dioxoisoindolin-2-yl)dodecylphosphonate (2.00 g, 4.43 mmol) was dissolved in dry dichloromethane (25 mL). Bromotrimethylsilane (1.8 mL, 14.2 mmol) was added via syringe. The reaction was capped with a greased glass stopper and allowed to stir overnight. 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 powdery solid (1.709 g, 98% yield). 1H NMR (400.14 MHz, DMSO) δ 7.84 (m, 4H), 3.54 (t, J=7.1 Hz, 2H), 1.58-1.53 (m, 2H), 1.50-1.31 (m, 4H), 1.30-1.20 (m, 16H). 13C {1H} NMR (100.62 MHz, DMSO) δ 167.9 (2C), 134.4 (2C), 131.6 (2C), 123.0 (2C), 37.36, 30.08 (d, J=15.8 Hz), 28.99, 28.95, 28.87 (2C), 28.70, 28.53, 27.85, 27.54 (d, J=136.5 Hz), 26.22, 22.73, (d, J=4.58 Hz). 31P {1H} NMR (161.97 MHz, DMSO): δ 27.74. MS (FAB, m/z): 396.2 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 396.19399 (396.19445). Analysis calculated (found) %: C 60.75 (60.64), H 7.65 (7.80).

Provenance & Evidence