Carbon Dioxide → HCID 67403142, compound

Participants

Reaction Steps

In a 100 ml round bottom flask, the fuming nitric acid was cooled to −45° C. using a dry ice/acetonitrile bath. 3.2054 g (10.2330 mmol, 1.0 eq) of the oxaborininol was dissolved in 2.5 mL of nitrobenzene. This solution was then added dropwise to the stirred and cooled nitric acid over a period of approximately 15 minutes. The reaction was allowed to stir for 45 minutes, recharging the acetonitrile and dry ice as needed. After 45 minutes, the reaction solution was poured over approximately 250 mL of wet ice. The mixture/suspension was allowed to warm to room temperature, stirring as it warmed (approximately 90 minutes). The aqueous mixture was then extracted with DCM (2×50 mL). The layers were separated and the organic layers were combined and washed with water to remove excess nitric acid (2×100 mL) until pH paper showed the water retained a neutral pH. The organic solution was then dried over MgSO4, filtered under vacuum, and then the solvent was removed under reduced pressure. The resultant yellow oil was then treated slowly with heptane, swirling as the solvent was added, until a yellow-white solid crashed out. The solid was then collected by filtration and washed with additional ice-cooled heptane. A yellow powder was isolated. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.47 (m, 4H) 3.14 (dd, J=10.98, 5.86 Hz, 1H) 3.88 (dt, J=11.21, 5.79 Hz, 1H) 4.13 (dd, J=11.03, 4.00 Hz, 1H) 7.57 (d, J=8.44 Hz, 1H) 8.27 (dd, J=8.42, 2.56 Hz, 1H) 8.48 (d, J=2.49 Hz, 1H) 8.95 (s, 1H).

Provenance & Evidence