Iodopentafluoroethane → N,N,N'-Trimethyl-N'-(2-nitro-4-pentafluoroethyl-phenyl)-propane-1,3-diamine

Participants

Reaction Conditions

Reaction Steps

To a pressure vessel was added N-(4-Bromo-2-nitro-phenyl)-N, N′,N′-trimethyl-propane-1,3-diamine (Step 1, 5.0 g, 15.8 mmol), copper powder (10.0 g, 158 mmol), and 20 mL DMSO. Pentafluoroethyl iodide (7.8 g, 31.6 mmol) was bubbled in and the vessel sealed. The mixture was then heated to 120° C. and vigorously stirred for 22 h. The reaction was cooled to 0° C. and filtered through a Buchner funnel, rinsing with EtOAc. The filtrate was then washed once with saturated aqueous NaHCO3, twice with water, once with brine, and then dried over Mg2SO4. The crude mixture was then purified by silica gel chromatography using a 10% MeOH/CH2Cl2 gradient to yield the title compound as a brown oil. MS (M+H)+=356; Calc'd 355.30 for C14H18F5N3O2.

Provenance & Evidence