J IRAN CHEM SOC
nanocatalyst (0.1 mmol) was pulverized in a mortar at room
temperature for an appropriate time. The reaction was mon-
itored by thin-layer chromatography (TLC). After comple-
tion of the reaction, CH Cl (5.0 mL) was then added to the
available reagents, high selectivity, recoverable catalyst,
high yields and environmentally benign protocol. The effi-
ciency and high activity of the present nanocatalyst were
confirmed by excellent isolated yields of the products
(Table 2) and several times reusability (Fig. 3).
2
2
mixture and filtered. Evaporation of the solvent followed
by recrystallization or column chromatography on silica
gel of the crude product gave the corresponding nitrated
compounds in good to excellent yields. The nanocatalyst
was simply separated from the reaction mixture by using an
external magnet, washed with methanol/diluted HCl solu-
tion and then dried in an oven at 60 °C. Before reusing the
recycled catalyst, it was weighted in any cycle, and after
that, it was reused in subsequent runs. Furthermore, fresh
catalyst was added to reciprocate decreased mass loss, if it
was considerable.
Acknowledgements The authors gratefully acknowledge the partial
support from the Research Council of the Iran University of Science
and Technology.
References
1
.
.
K. Schofield, Aromatic Nitration (University Press, Cambridge,
980)
G.A. Olah, R. Malhotra, S.C. Narang, Nitration: Methods and
Mechanisms (VCH, New York, 1989)
1
2
Spectral data of the selected products
3. M.A. Zolfigol, E. Madrakian, E. Ghaemi, Molecules 7, 734
2002)
(
4
.
A. Khalafi-Nezhad, A. Parhami, M.N. Soltani Rad, M.A. Zolf-
igol, A. Zare, Tetrahedron Lett. 48, 5219 (2007)
P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Curr. Org.
Chem. 10, 2171 (2006)
4
1
-Nitrophenol (Table 2, entry 9): Yellow solid; m.p.
09–111 °C. IR (KBr) 1338, 1494, 1546, 3320 cm . H
−1 1
5
.
NMR (300 MHz, CDCl ) δ (ppm) 6.17 (s, 1H, OH), 6.93
3
1
3
6. M.A. Zolfigol, B.F. Mirjalili, A. Bamoniri, M. Zarchi, A. Karimi,
(
(
d, J = 9.0 Hz, 2H), 8.17 (d, J = 9.0 Hz, 2H). C NMR
A. Zarei, L. Khazdooz, J. Noei, Bull. Korean Chem. Soc. 25,
75 MHz, CDCl ) δ (ppm) 115.7, 126.3, 141.3, 161.3.
3
1
414 (2004)
4
-Bromo-2-nitrophenol (Table 2, entry 12): Yellow solid;
7
. M.A. Zolfigol, Tetrahedron 57, 9509 (2001)
−
1 1
m.p. 80–83 °C. IR (KBr) 1313, 1527, 3273 cm . H NMR
8. G. Chehardoli, M.A. Zolfigol, S.B. Azimi, E. Alizadeh, Chin.
Chem. Lett. 22, 827 (2011)
(
(
(
300 MHz, CDCl ) δ (ppm) 7.07 (d, J = 8.7 Hz, 1H), 7.66
3
9
.
K. Smith, A. Musson, G.A. DeBoos, J. Org. Chem. 63, 8448
1998)
d, J = 8.7 and 2.4 Hz, 1H), 8.24 (d, J = 2.1 Hz, 1H), 10.49
(
1
3
s, 1H, OH). C NMR (75 MHz, CDCl ) δ (ppm) 111.7,
3
10. S.N. Nagy, J. Phys. Org. Chem. 7, 385 (1994)
1
21.7, 127.3, 140.3, 142.9, 154.1.
-Nitronaphthalene (Table 2, entry 20): Yellow solid;
11. F. Nemati, H. Kiani, Chin. Chem. Lett. 21, 405 (2010)
1
2. A. Ghorbani-Choghamarani, H. Goudarziafshar, M. Nikoorazm,
1
Z. Naseri, Chin. Chem. Lett. 22, 1434 (2011)
−
1
1
m.p. 53–56 °C. IR (KBr) 1336, 1519 cm . H NMR
1
3. F. Nemati, R. Saeedirad, Chin. Chem. Lett. 24, 370 (2013)
(
7
300 MHz, CDCl ) δ (ppm) 7.54 (t, J = 7.8 Hz, 1H),
3
14. J. Safari, Z.J. Zarnegar, Mol. Catal. A 379, 269 (2015)
15. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, M. Saeedi, F.F. Bamo-
harram, Monatsh. Chem. 138, 449 (2017)
.62 (t, J = 7.2 Hz, 1H), 7.72 (t, J = 6.9 Hz, 1H), 7.96
(
d, J = 8.1 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 8.23 (d,
J = 7.5 Hz, 1H), 8.56 (d, J = 8.7 Hz, 1H). C NMR
75 MHz, CDCl ) δ (ppm) 123.5, 124.4, 124.5, 125.5,
1
6. A. Maleki, Tetrahedron 68, 7827 (2012)
1
3
1
7. A. Maleki, Tetrahedron Lett. 54, 2055 (2013)
(
3
18. A. Maleki, M. Kamalzare, Catal. Commun. 53, 67 (2014)
19. A. Maleki, R. Paydar, RSC Adv. 5, 33177 (2015)
1
27.7, 129.0, 129.8, 134.7, 135.0.
,4-Dinitro-1H-imidazole (Table 2, entry 21): Yellow
solid; m.p. 93–95 °C. IR (KBr) 1245, 1517, 1557, 1638,
2
2
0. A. Maleki, M. Aghaei, N. Ghamari, Chem. Lett. 44, 259 (2015)
1. A. Maleki, Z. Alrezvani, S. Maleki, Catal. Commun. 69, 29
1
(
2015)
−
150 cm . H NMR (300 MHz, CDCl ) δ (ppm) 9.43 (s,
3
1 1
3
1
1
22. A. Maleki, H. Movahed, R. Paydar, RSC Adv. 6, 13657 (2016)
23. A. Maleki, H. Movahed, P. Ravaghi, Carbohydr. Poly. 156, 259
1
3
H), 8.99 (s, 1H). C NMR (75 MHz, CDCl ) δ (ppm)
3
(
2017)
20.0, 133.2, 147.2.
2
4. V.S.P. Ganjala, ChKP Neeli, ChV Pramod, M. Khagga, K.S.R.
Rao, D.R. Burri, Catal. Commun. 49, 82 (2014)
2
5. A.R. Hajipour, A.E. Ruoho, Tetrahedron Lett. 46, 8307 (2005)
Conclusion
26. N. Nowrouzi, M. Zareh Jonaghani, Tetrahedron Lett. 52, 5081
2011)
7. T.N. Parac-Vogt, K. Binnemans, Tetrahedron Lett. 45, 3137
2004)
8. Y. Yuan, J. Nie, Z. Zhang, S. Wang, Appl. Catal. A 295, 170
(2005)
(
2
2
2
3
In summary, we have described a simple, rapid and con-
venient method for the nitration of aromatic compounds
in the presence of SO H-functionalized silica-coated mag-
netic core/shell nanoparticles as a nanocomposite catalyst
along with sodium nitrate under solvent-free conditions at
room temperature. The superiorities of the present method
over previous reports include a very rapid reaction, readily
(
3
9. R.R. Yadav, R.A. Vishwakarma, S.B. Bharate, Tetrahedron Lett.
5
3, 5958 (2012)
0. R.E. March, M.R. Weir, F.A. Londry, S. Catinella, P. Traldi, J.A.
Stone, W.B. Jacobs, Can. J. Chem. 72, 966 (1994)
31. J. Liu, J. Li, J. Ren, B. Zeng, Tetrahedron Lett. 55, 1581 (2014)
1
3