Toluene was distilled from the mixture of potassium fluoride (38.2 g, 657 mmol), cetrimide (5.94 g, 17.6 mmol), DMF (250 mL), and dry toluene (100 mL) to remove traces of moisture. 2,4,5- Trichloronitrobenzene (7) (50.0 g, 220 mmol) was added and heated at 125 ??C for 12 h under N2. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and evaporated to give a residue, which was distilled under vacuo to provide 9 (23.5 g, 55%). bp = 83 ??C at 0.5 Torr, lit. bp) 85 ??C at 0.5 Torr; 1H NMR (CDCl3, 200 MHz) |? 7.18 (t, 1 H, J = 9.2 Hz), 8.24 (t, 1 H, J = 7.4 Hz).