3298
U. B. Patil et al.
PAPER
+
GC-MS: m/z (%) = 131 (M , 100), 104 (52), 30 (58).
Acknowledgment
3
-Chlorobenzonitrile18
The authors are thankful to UGC-SAP, New Delhi, India for the
award of fellowship.
Crystalline white; yield: 0.123 g (90%); mp 38–40 °C.
1
H NMR (300 MHz, CDCl ): δ = 7.65–7.58 (d, 2 H), 7.56–7.27 (d,
3
2
H).
Supporting Information for this article is available online at
13
C NMR (100 MHz, CDCl ): δ = 135.1, 133.1, 131.8, 130.3, 117.3,
3
http://www.thieme-connect.com/ejournals/toc/synthesis.SnoIufproi
m
tgioSrantnugIifoop
r
itmnatr
113.8.
+
GC-MS: m/z (%) = 137 (M , 100), 139 (33), 102 (36), 75 (20), 50
References
(15).
-Chlorobenzonitrile18
(1) (a) Gu, X.-H.; Wan, X. Z.; Jiang, B. Bioorg. Med. Chem.
Lett. 1999, 9, 569. (b) Chihiro, M.; Nagamoto, H.;
4
White solid; yield: 0.122 g (89%); mp 90–93 °C.
Tekemura, I.; Kitano, K.; Komatsu, H.; Sekiguchi, K.;
Tabusa, F.; Mori, T.; Tominaga, M.; Yabuuchi, Y. J. Med.
Chem. 1995, 38, 353. (c) Jnaneshwara, G. K.; Deshpande, V.
H.; Lalithambika, M.; Ravindranathan, T.; Bedekar, A. V.
Tetrahedron Lett. 1998, 39, 459. (d) Wittenberger, S. J.;
Donner, B. G. J. Org. Chem. 1993, 58, 4139. (e) Bailey, T.
R.; Diana, G. D.; Kowalczyk, P. J.; Akullian, V.; Eissenstat,
M. A.; Cutcliffe, D.; Mallamo, J. P.; Carabateas, P.; Pevear,
D. C. J. Med. Chem. 1992, 35, 4628. (f) Kadaba, P. K.
Synthesis 1973, 71. (g) Moody, C. J.; Doyle, K. J. Prog.
Heterocycl. Chem. 1997, 9, 1. (h) Ducept, P. C.; Marsden, S.
P. Synlett 2000, 692.
1
H NMR (300 MHz, CDCl ): δ = 7.65–7.58 (d, 2 H), 7.49–7.27 (d,
H).
3
2
13
C NMR (100 MHz, CDCl ): δ = 139.5, 133.3, 129.6, 117.9, 110.7.
3
+
GC-MS: m/z (%) = 137 (M , 100), 139 (33), 102 (36), 75 (20), 50
(
15).
4
-Bromobenzonitrile26b
White solid yield: 0.165 g (91%); mp 110–112 °C.
1
H NMR (300 MHz, CDCl ): δ = 7.67–7.62 (d, 2 H), 7.55–7.27 (d,
3
2
H).
13
C NMR (100 MHz, CDCl ): δ = 133.3, 132.6, 127.9, 118.0, 111.1.
3
(2) (a) Larock, R. C. Comprehensive Organic Transformations,
2nd ed.; Wiley-VCH: New York, 1999, 1949–1950, 1955,
1983-1985. (b) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
+
GC-MS: m/z (%) = 181 (M , 71), 182 (69), 102 (100), 75 (36), 50
(
23).
(
c) Fleming, F. F.; Yaot, L.; Ravikumart, P. C.; Funk, L.;
3
-Fluorobenzonitrile26a
Shook, B. C. J. Med. Chem. 2010, 53, 7902. (d) Herr, R. J.
Bioorg. Med. Chem. 2002, 10, 3379.
Colorless liquid; yield: 0.107 g (89%); bp 182–183 °C.
1
H NMR (300 MHz, CDCl ): δ = 7.48–7.46 (d, 2 H), 7.55–7.27 (d,
(3) (a) The Chemistry of the Cyano Group; Rappoport, Z., Ed.;
Interscience: New York, 1970. (b) Larock, R. C.
3
2
H).
+
Comprehensive Organic Transformations; VCH: New
York, 1989. (c) Kleemann, A.; Engel, J.; Kutscher, B.;
Reichert, D. Pharmaceutical Substances: Synthesis Patents,
Applications, 4th ed.; Georg Thieme: Stuttgart, 2001.
(d) Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34,
GC-MS: m/z (%) = 121 (M , 100), 94 (31), 75 (7), 50 (8).
3
-Cyanopyridine13
Off-white solid; yield: 0.084 g (81%); mp 48–52 °C.
1
H NMR (300 MHz, CDCl ): δ = 8.91 (s, 1 H), 8.84 (d, 1 H), 7.98
3
5
63.
(d, 1 H), 7.46 (dd, 1 H).
(
(
4) Mowry, D. T. Chem. Rev. 1948, 42, 189.
5) (a) Semmelhack, M. F.; Schmid, C. R. J. Am. Chem. Soc.
+
GC-MS: m/z (%) = 104 (M , 100), 77 (68), 50 (25).
1
983, 105, 6732. (b) Chen, F. E.; Kuang, Y. Y.; Dai, H. F.;
Phenylacetonitrile13
Lu, L.; Huo, M. A. Synthesis 2003, 2629. (c) Baxendale, I.
R.; Ley, S. V.; Sneddon, F. H. Synlett 2002, 775. (d) Wu, J.
D.; Chu, C. M.; Yao, C. F.; Shia, K. S. Chem. Commun.
2007, 301. (e) Phillips, B. A.; Fodor, G.; Gal, J.; Letourneau,
F.; Ryan, J. J. Tetrahedron 1973, 29, 3309. (f) Lee, J. C.;
Yoon, J. M.; Baek, J. W. Bull. Korean Chem. Soc. 2007, 28,
Colorless liquid; yield: 0.091 g (77%); bp 233–234 °C.
1
H NMR (300 MHz, CDCl ): δ = 7.35–7.31 (m, 5 H), 3.74 (s, 2 H).
3
+
GC-MS: m/z (%) = 117 (M , 100), 90 (59), 63 (12), 51 (12).
(
4-Chlorophenyl)acetonitrile16b
Colorless liquid; yield: 0.122 g (81%); bp 265–267 °C.
2
9.
1
H NMR (300 MHz, CDCl ): δ = 7.38–7.32 (m, 4 H), 3.77 (s, 2 H).
(6) Brackman, W.; Smith, P. Recl. Trav. Chim. Pays–Bas 1963,
82, 757.
7) Parameswaran, K. N.; Friedman, O. M. Chem. Ind. (London)
3
+
GC-MS: m/z (%) = 151 (M , 24), 116 (100), 89 (19).
(
3-Methoxyphenyl)acetonitrile26d
1965, 988.
(
Colorless liquid; yield: 0.128 g (87%); bp 164–165 °C.
(8) Bose, D. S.; Narsaiah, A. V. Tetrahedron Lett. 1998, 39,
1
6533.
H NMR (300 MHz, CDCl ): δ = 7.28–7.25 (m, 1 H), 6.91–6.86 (m,
3
(
9) Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron
Lett. 2000, 41, 6749.
10) Talukdar, S.; Hsu, J.-L.; Chou, T.-C.; Fang, J.-M.
Tetrahedron Lett. 2001, 42, 1103.
3
H), 3.71 (s, 2 H), 3.81 (s, 3 H).
+
GC-MS: m/z (%) = 147 (M , 100), 132 (25), 117 (21), 90 (19), 77
(
(
(
(46).
11) Bandgar, B. P.; Makone, S. S. Synth. Commun. 2006, 36,
Propionitrile26e
Colorless liquid; yield: 0.0385 g (70%); bp 265–267 °C.
1
347.
12) Arote, N. D.; Bhalerao, D. S.; Akamanchi, K. G.
Tetrahedron Lett. 2007, 48, 3651.
(13) Telvekar, V. N.; Patel, K. N.; Kundiakar, H. S.; Chaudhari,
1
H NMR (300 MHz, CDCl ): δ = 1.29 (m, 3 H), 2.36 (m, 2 H).
3
+
GC-MS: m/z (%) = 54 (M , 100), 51 (13), 40 (5).
H. K. Tetrahedron Lett. 2008, 49, 2213.
(14) Barahman, M.; Salman, S. Tetrahedron Lett. 2005, 46, 6923.
Synthesis 2013, 45, 3295–3299
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