Molecules 2013, 18
405
1
9
7
1
2
-Bromoanthracene (11). H-NMR: 8.88 (s, 1H), 8.46 (d, J = 7.2 Hz, 2H), 8.03 (d, J = 7.2 Hz, 2H),
1
3
.78 (dd, J = 7.2 Hz, J = 8.1 Hz, 2H), 7.62 (dd, J = 7.2 Hz, J = 8.1 Hz, 2H). C-NMR: 133.91,
30.99, 129.71, 128.47, 126.13, 125.21, 122.93. GC-MS: m/z (%) = 88 (89), 176 (90), 256 (M , 99),
+
+
58 (M +2, 100).
1
1
-Chloroanthra-9,10-quinone (12). H-NMR: 8.14 (d, J = 8.1 Hz, 2H), 7.92 (d, J = 8.1 Hz, 2H), 7.76
1
3
(
m, 3H). C-NMR: 182.42, 181.79, 138.12, 135.56, 134.20, 131.34, 130.70, 129.34, 128.47, 127.43,
4.57, 45.21. GC-MS: m/z (%) = 186 (78), 214 (100), 241 (M , 92, 243 (M +2, 28).
+
+
4
1
13
Toluene (13). H-NMR: 7.55–7.61 (m, 5H), 2.75 (s, 3H). C-NMR: 137.83, 129.14, 128.29,
1
+
+
25.58, 21.18. GC-MS: m/z (%) = 65 (16), 91 (M −1, 100), 92 (256 M ).
1
13
Pyridine (14). H-NMR: 8.31 (d, J = 5.9 Hz, 2H), 7.27–7.31 (m, 1H), 6.88–6.96 (m, 2H). C-NMR:
+
149.11, 134.98, 123.11. GC-MS: m/z (%) = 52 (89), 79 (M , 100).
1
3
-Bromopyridine (15). H-NMR: 8.66 (d, J = 7.6 Hz, 1H), 8.47 (s, 1H), 7.77 (d, J = 7.7 Hz, 1H), 7.14
13
(
d, J = 7.6 Hz, 1H). C-NMR: 151.00, 147.80, 138.39, 124.55, 120.78. GC-MS: m/z (%) = 51 (33),
8 (100), 157 (M , 28), 159 (M +2, 30).
+
+
7
1
2
-Chloropyridine (16). H-NMR: 8.44 (d, J = 8.4 Hz, 1H), 7.70 (dt, J = 7.7 Hz, J = 7.3 Hz, 1H), 7.39
13
(
d, J = 7.4 Hz, 1H), 7.28 (dt, J = 7.3 Hz, J = 7.4 Hz, 1H). C-NMR: 151.39, 149.65, 138.64, 124.33,
22.18. GC-MS: m/z (%) = 51 (40), 78 (100), 113 (M , 89), 115 (M +2, 28).
+
+
1
1
2
-Fluoro-5-(trifluoromethyl)pyridine (18). H-NMR: 8.21 (s, 1H), 7.98 (d, J = 5.8 Hz, 1H), 7.16 (d,
1
3
J = 5.8 Hz, 1H). C-NMR: 162.03, 147.19, 139.08, 128.08, 124.77, 108.37. GC-MS: m/z (%) = 115
+
(
52), 146 (78), 165 (M , 100).
1
13
3
-Chloro-2-(trifluoromethyl)pyridine (19). H-NMR: 8.41 (s, 2H), 7.90 (s, 1H). C-NMR: 150.09,
+
1
46.56, 137.48, 133.92, 125.73, 124.77. GC-MS: m/z (%) = 69 (38), 146 (42), 181 (M , 100), 183
+
(
M +2, 24).
1
2
-Bromothiophene (20). H-NMR: 7.14 (dd, J = 7.1 Hz, J = 7.0 Hz, 1H), 6.99 (dd, J = 7.0 Hz, J = 6.9 Hz,
1
3
1
H), 6.80 (dd, J = 7.1 Hz, J = 6.9 Hz, 1H). C-NMR: 129.88, 127.68, 127.02, 112.21. GC-MS: m/z
%) = 57 (29), 83 (80), 162 (M , 99), 164 (M +2, 100).
+
+
(
1
2
-Iodothiophene (21). H-NMR: 7.18 (dd, J = 7.1 Hz, J = 7.0 Hz, 1H), 7.03 (dd, J = 7.0 Hz, J = 6.9 Hz,
1
3
1
H), 6.83 (dd, J = 7.1 Hz, J = 6.9 Hz, 1H). C-NMR: 130.22, 128.02, 127.36, 112.55. GC-MS: m/z
%) = 83 (52), 126 (16), 210 (M , 100).
+
(
4
. Conclusions
Dehalogenation of haloaromatics and haloheteroaromatics in an ionic liquid were successfully
accomplished. Although the scope and limitations of this new method have not been fully established,
it is a promising candidate for use as an alternative solution for the dehalogenation of aromatic or
heteroaromatic intermediates. Besides, it constitutes an inexpensive method that avoids the use of other