MAHANTA ET AL.
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FIGURE 5 Schematic diagram of the
reaction mechanism
4‐Hydroxynitrobenzene (entry 7, Table 2): White solid
(119 mg, 85%); m.p. 270–275°C; 1H NMR (400 MHz,
CDCl3, δ, ppm): 8.18 (d, J = 9.2 Hz, 2H), 6.94 (d,
J = 8 Hz, 2H), 6.66 (1H, br s); 13C NMR (100 MHz,
CDCl3, δ, ppm): 161.7, 141.5, 126.4, 115.8.
4‐Aminonitrobenzene (entry 8, Table 2): Yellow solid
(237 mg, 89%); m.p. 330–335 C; 1H NMR (400 MHz,
acetone‐d6, δ, ppm): 7.95 (d, J = 6.8 Hz, 2H), 6.70 (d,
J = 7.2 Hz, 2H), 6.03 (br s, 1H); 13C NMR (100 MHz,
CDCl3, δ, ppm): 155.2, 137.3, 126.1, 112.7.
4‐Methoxynitrobenzene (entry 9, Table 2): White solid
(242 mg, 86%); m.p. 50–53°C; 1H NMR (400 MHz, CDCl3,
δ, ppm): 8.22–8.19 (d, J = 9.2 Hz, 2H), 6.96 (d, J = 7.2 Hz,
2H), 3.91 (s, 3H); 13C NMR (100 MHz, CDCl3, δ, ppm):
164.6, 141.5, 126.0, 114.0, 56.0.
2‐Methylnitrobenzene (entry 10, Table 2): Yellow
liquid (107 mg, 78%); 1H NMR (400 MHz, CDCl3, δ,
ppm): 7.13–7.09 (m, 1H), 6.75–6.73 (m, 1H), 6.65–6.62
(m, 2H), 2.29 (s, 3H); 13C NMR (100 MHz, CDCl3, δ,
ppm): 155.5, 139.9, 129.5, 121.6, 116.1, 112.3, 21.4.
4‐Methylnitrobenzene (entry 11, Table 2): White solid
(110 mg, 81%); m.p. 50–55°C; 1H NMR (400 MHz, CDCl3,
δ, ppm): 8.11 (d, J = 8.8 Hz, 2H), 7.33–7.27 (m, 2H), 2.46
(s, 3H); 13C NMR (100 MHz, CDCl3, δ, ppm): 146.1, 129.9,
123.5, 21.7.
CDCl3, δ, ppm): 7.93–7.92 (m, 1H), 7.56–7.55 (m, 1H),
7.40–7.39 (m, 1H); 13C NMR (100 MHz, CDCl3, δ, ppm):
132.6, 128.6, 127.5, 127.0, 126.9.
3‐Methoxy‐2‐nitropyridine (entry 13, Table 2): White
solid (123 mg, 80%); m.p. 75–80°C; 1H NMR
(400 MHz, CDCl3, δ, ppm): 8.41–8.40 (m, 1H), 8.29–
8.28 (m, 1H), 7.07–7.04 (m, 1H), 4.12 (s, 3H); 13C
NMR (100 MHz, CDCl3, δ, ppm): 156.6, 151.8, 135.1,
134.0, 116.5, 54.8.
4‐Fluoronitrobenzene (entry 14, Table 2): Yellow liq-
1
uid (121 mg, 86%); H NMR (400 MHz, CDCl3, δ, ppm):
8.28 (d, J = 8 Hz, 2H), 7.24 (d, J = 8 Hz, 2H), 7.39–7.36
(m, 2H); 13C NMR (100 MHz, CDCl3, δ, ppm): 167.6,
165.0, 144.4, 126.4, 126.3, 116.5, 116.3.
2,4‐Diflouronitrobenzene (entry 15, Table 2): Yellow
solid (136.74 mg, 86%); m.p. 12–15°C; 1H NMR
(400 MHz, CDCl3, δ, ppm): 8.19–8.17 (m, 1H), 7.09–7.05
(m, 2H); 13C NMR (100 MHz, CDCl3, δ, ppm): 167.1,
164.4, 134.1, 128.3, 128.27, 112.2, 106.6.
2‐Chloronitrobenzene (entry 16, Table 2): Yellow solid
(131.88 mg, 84%); m.p. 30–33°C; 1H NMR (400 MHz,
CDCl3, δ, ppm): 7.87–7.85 (m, 1H), 7.56–7.53 (m, 2H),
7.45–7.40 (m, 2H); 13C NMR (100 MHz, CDCl3, δ, ppm):
148.1, 133.2, 131.9, 127.4, 125.6.
4‐Chloronitrobenzene (entry 17, Table 2): Yellow solid
(138 mg, 88%); m.p. 80–85°C; 1H NMR (400 MHz, CDCl3,
δ, ppm): 8.79 (d, J = 8.4 Hz, 2H), 7.52 (d, J = 9.2 Hz, 2H);
2‐Thiophenylnitrobenzene (entry 12, Table 2): White
1
solid (107 mg, 83%); m.p. 40–45°C; H NMR (400 MHz,