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Transition Met Chem (2011) 36:1–11
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4-Phenoxybenzonitrile (4c). Oil [51]. H NMR (CDCl3,
resulting residue was purified by column chromatography on
silica gel to provide the desired product. The product was
purified by column chromatography, and its identity con-
firmed by comparison of color and NMR spectra with those
reported in the literature or authentic samples from our
laboratories.
400 MHz) d: 7.57 (d, J = 8.6 Hz, 2H), 7.42 (t,
J = 7.9 Hz, 2H), 7.25 (t, J = 7.6 Hz, 1H), 7.0 (d,
J = 7.9 Hz, 2H), 6.89 (d, J = 8.8 Hz, 2H); 13C NMR
(CDCl3, 100 MHz) d: 160.4, 151.1, 135.8, 131.5, 123.0,
118.4, 116.5, 120.3, 101.5.
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4-Methyl-diphenylether (4d). Colorless liquid [49]. H
NMR (CDCl3, 400 MHz) d: 2.41 (s, 3H), 7.00 (d,
J = 8.0 Hz, 2H), 7.03–7.3 (m, 2H), 7.10–7.17 (m, 1H),
7.24 (d, J = 8.4 Hz, 2H), 7.35 (t, J = 8.4 Hz, 2H); 13C
NMR (CDCl3, 100 MHz) d: 20.4, 118.3, 119.6, 122.8,
129.8, 130.1, 133.0, 154.2, 157.9.
Characterization of the used catalyst
Characterization of the used catalyst was done by IR and
UV–vis spectroscopic data. The FTIR spectrum of the used
catalyst was identical to that of the original catalyst. Thus,
for the used Cat-1, peaks at 1,618 cm-1 (for pyridine ring),
1,313 cm-1 (vC–O, coordinated), a weak peak at 547 cm-1
(vCu–N) and a Cu–O stretching vibration at 431 cm-1
were all present in the spectrum. In Cat-2, a peak at
1,250 cm-1 (for –CH2Cl), 1,312 cm-1 (vC–O, coordi-
nated), a weak peak at 542 cm-1 (vCu–N) and a Cu–O
stretching vibration at 433 cm-1 were all present in the
spectrum of the used Cat-2. The UV–vis spectra of the used
catalysts were also very similar to those of the original
catalysts. From the spectroscopic data, we conclude that
the structures of the used catalysts are identical with those
of the original.
4-Cyano-4-methoxy-diphenylether (4e). White solid
[52]. 1H NMR (CDCl3, 400 MHz) d: 3.76 (s, 3 H),
6.84–6.87 (m, 4H), 6.91–6.94 (m, 2H), d 7.47–7.51 (m,
2H); 13C NMR (CDCl3, 100 MHz) d: 55.7, 105.4, 115.2,
117.31, 119.15 122, 134.2, 148, 157.2, 162.5.
4’-Methyl-4-phenoxy-phenylacetate (4f). White Solid
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[53]. H NMR (CDCl3, 400 MHz) d: 8.00–8.04 (2H, d,
J = 8.4), 7.18–7.20 (2H, d, J = 8.3), 6.95–6.96 (4H, m),
3.88 (3H, s) and 2.34 (3H, s); 13C NMR (CDCl3, 100 MHz)
d: 166.7, 162.6, 153.0, 134.0, 131.6, 130.7, 124.5, 120.3,
117.1, 52.0, 21.0.
1-(4-nitrophenoxy)-4-methoxybenzene (4g). Off-white
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solid [54]. H NMR (CDCl3, 400 MHz) d: 3.84 (s, 3H),
6.91 (d, J = 8.8 Hz, 2H), 7.05 (d, J = 10.3 Hz, 2H), 7.10
(d, J = 8.8 Hz, 2H), 8.16 (d, J = 8.1 Hz, 2H); 13C NMR
(CDCl3, 100 MHz) d: 55.6, 113.3, 117.7, 118.1, 119.0,
139.4, 149.3, 153.8, 163.0.
Characterization of the products
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All H and 13C NMR spectra were recorded at 400 and
1-(4-nitrophenoxy)-4-bromobenzene (4h). Yellow solid
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100 MHz, respectively. The characterizations of the prod-
ucts were carried out by 1H NMR spectroscopy using
Bruker DPX-400 in CDCl3 with TMS as internal standard.
Chemical shifts are given as d values with reference to
tetramethylsilane (TMS) as the internal standard. The
reaction products were quantified (GC data) by Varian
3400 gas chromatograph equipped with a 30 m CP-
SIL8CB capillary column and a flame ionization detector
and identified (GC–MS) by Trace DSQ II GC–MS equip-
ped with a 60-m TR-50MS capillary column. Standardi-
zation of the products was done by calibration using
dihexyl ether as internal standard. Color, 1H and 13C NMR
data of all the products are given below.
[54]. H NMR (CDCl3, 400 MHz) d: 6.98 (d, J = 8.9 Hz,
2H), 7.00 (d, J = 9.3 Hz, 2H), 7.51 (d, J = 8.9 Hz, 2H),
8.22 (d, J = 9.1 Hz, 2H); 13C NMR (CDCl3, 100 MHz) d:
113.0, 118.4, 120.1, 121.0, 139.2, 155.4, 163.3.
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2-Methyl-diphenylether (4i). Colorless liquid [49]. H
NMR (CDCl3, 400 MHz) d: 2.19 (s, 3H), 6.87–6.91 (m, 3H),
6.97–7.07 (m, 2H), 7.12–7.165 (m, 1H), 7.19–7.30 (m, 3H);
13C NMR (CDCl3, 100 MHz) d: 16.1, 117.6, 119.7, 122.0,
124.0, 127.3, 129.6, 130.1, 131. 2, 154.7, 158.0.
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2-Methoxy-diphenylether (4j). Colorless liquid [55]. H
NMR (CDCl3, 400 MHz) d: 3.77 (s, 3H), 6.81–6.90 (m,
3H), 6.91–6.94 (m, 1H), 6.96–7.02 (m, 2H), 7.03–7.10 (m,
1H), 7.16–7.25 (m, 2H); 13C NMR (CDCl3, 100 MHz) d:
56, 112.9, 117.3, 121.1, 121.2, 122.6, 124.9, 129.6, 145.1,
151.6, 158.
Diphenylether (4a). Colorless liquid [49]. 1H NMR
(CDCl3, 400 MHz) d: 7.07–7.14 (m, 4H), 7.13–7.20 (m,
2H); 7.41–7.45 (m, 4H); 13C NMR (CDCl3, 100 MHz) d:
116, 124.4, 128.7, 157.0.
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Acknowledgments We thank the Department of chemistry, Uni-
versity of Calcutta, for providing us the instrumental support. We
gratefully acknowledge DST, New Delhi, for award of grant under its
FIST program to the Department of Chemistry, University of Kalyani.
SMI acknowledge the following agencies for funding: DST, CSIR and
UGC, New Delhi, India.
4-Nitro-diphenylether (4b). Yellow solid [50]. H NMR
(CDCl3, 400 MHz) d: 6.98–7.00 (m, 2H), 7.04–7.10 (m,
2H), 7.20–7.28 (m, 1H), 7.41–7.44 (m, 2H), 8.14–8.20 (m,
2H); 13C NMR (CDCl3, 100 MHz) d: 117.4, 121.2, 125.7,
127, 129.4, 142.2, 153.9, 163.2.
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