[C:1]([C:5]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=1N)([CH3:4])([CH3:3])[CH3:2].Cl.N([O-])=O.[Na+].[H+].[F:21][P-](F)(F)(F)(F)F>O>[C:1]([C:5]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=1[F:21])([CH3:4])([CH3:3])[CH3:2]To a stirred solution of 2-tert-butyl-5-nitro-aniline (5.0 g, 25.74 mmol) in H2O (20 mL) was added conc. HCl (10 mL). Once dissolved, the mixture was cooled to 0° C. followed by the slow addition of NaNO2 (1.8 g, 819 μL, 25.74 mmol) in H2O (10 mL). The reaction mixture was stirred at 0° C. for another 0.5 h. Then HPF6 solution was added (2×20 mL) batch wise. The precipitate formed was obtained by filtration, which was then heated under infrared light at approximately 130-150° C. The grey solid slowly turned to a dark viscous oil, which was purified by silica gel column chromatography to afford 1-tert-butyl-2-fluoro-4-nitrobenzene (0.6 g, 12%). 1H NMR (400 MHz, CDCl3) δ 7.96 (dd, J=2.4, 8.8 Hz, 1H), 7.87 (dd, J=2.4, 12.0 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 1.43 (s, 9H).
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