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Green Chemistry
Benzenesulfonyl bromide (3a). Colorless oil (0.38 g, 96%).
503–507, pp. 736–739; (b) P. J. Kociensky, Protecting Groups,
Thieme, New York, 1994, 96–102; (c) G. Theodoridis, Tetra-
hedron, 2000, 56, 2339–2358.
1H NMR (300 MHz, CDCl3): δ = 8.02–7.99 (m, 2H), 7.76 (t, J =
7.3 Hz, 1H), 7.63 (t, J = 7.7 Hz, 2H); 13C NMR (75 MHz, CDCl3):
δ = 136.4, 133.6, 131.3, 129.3, 128.7, 127.4; IR (neat): ν 3022,
2919, 1489, 1329, 1143, 806, 653 cm−1. EI-MS 220, 171, 158,
137, 97, 69; EI-HRMS: exact mass observed for C6H5ClO2S:
219.91920 (calculated: 219.91936).
2 (a) J. H. Brewster and C. J. Ciotti, J. Am. Chem. Soc., 1955,
77, 6214–6215; (b) G. Blotny, J. F. Biernat and E. Taschner,
Liebigs Ann. Chem., 1963, 663, 195–207; (c) J. D. Moore,
R. H. Herpel, J. R. Lichtsinn, D. L. Flynn and P. R. Hanson,
Org. Lett., 2003, 5, 105–107; (d) S. R. Dubbaka and P. Vogel,
J. Am. Chem. Soc., 2003, 125, 15292–15293; (e) L. Kvaeno,
M. Werder, H. Hauser and E. M. Carreira, Org. Lett., 2005,
7, 1145–1149; (f) G. Lassalle, D. Galtier and F. Galli, EP,
643047, 1995; (g) O. M. Lezina, A. V. Kuchin and
S. A. Rubtsova, RU, 2289574, 2006.
3 (a) K. Bahrami, M. M. Khodaei and M. Soheilizad, Synlett,
2009, 2773–2776; (b) H. Veisi, A. Sedrpoushan, S. Hemmati
and D. Kordestani, Phosphorus, Sulfur Silicon Relat. Elem.,
2011, 186, 213–216; (c) O. M. Lezina, S. A. Rubtsova and
A. V. Kuchin, Russ. J. Org. Chem., 2011, 47, 1249–1251.
4 K. Bahrami, M. M. Khodaei and M. Soheilizad, J. Org.
Chem., 2009, 74, 9287–9291.
5 K. Bahrami, M. M. Khodaei and J. Abbasi, Synthesis, 2012,
316–322.
6 K. Bahrami, M. M. Khodaei, M. Soheilizad and K. Donya,
Tetrahedron Lett., 2012, 53, 354–358.
7 G. K. S. Prakash, T. Mathew, C. Panja and G. A. Olah, J. Org.
Chem., 2007, 17, 5847–5850.
8 B. Grzegorz, Tetrahedron Lett., 2003, 44, 1499–1501.
9 G. K. Joong and J. K. K. Doo, Synlett, 2010, 3049–3052.
4-Chlorobenzene-1-sulfonyl bromide (3b). White solid
(0.35 g, 95%). 1H NMR (300 MHz, CDCl3): δ = 7.98 (d, J =
8.6 Hz, 2H), 7.60 (d, J = 8.6 Hz, 2H); 13C NMR (75 MHz,
CDCl3): δ = 142.4, 140.4, 130.0; IR (neat): ν 3109, 3052, 1573,
1474, 1184, 1088, 825, 755, 559 cm−1. EI-MS 256, 254, 177,
175, 113, 111, 75, 76; EI-HRMS: exact mass observed for
C6H4Cl2O2S: 253.87998 (calculated: 253.88039).
3-Fluorobenzene-1-sulfonyl bromide (3c). Colorless oil
(0.34 g, 92%). 1H NMR (300 MHz, CDCl3): δ = 7.84–7.80 (m, 2H),
7.72–7.60 (m, 2H), 7.49–7.43 (m, 1H); 13C NMR (75 MHz,
CDCl3): δ = 163.5, 131.4, 122.7, 122.4, 114.1, 113.7; IR (neat):
ν 3073, 2938, 1564, 1485, 1378, 1192, 846 cm−1. EI-HRMS: exact
mass observed for C6H4BrFO2S: 237.9096 (calculated: 237.9099).
4-Methylbenzene-1-sulfonyl chloride (3d). White solid
(0.33 g, 89%). 1H NMR (300 MHz, CDCl3): δ = 7.87 (d, J =
8.0 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H); 13C NMR
(75 MHz, CDCl3): δ = 142.20, 136.81, 130.06, 126.40, 21.80;
IR (KBr): ν 3010, 2923, 1584, 1457, 1027, 696 cm−1. EI-MS 234,
202, 186, 171, 139, 123, 107, 92, 77; EI-HRMS: exact mass
observed for C7H7BrO2S: 233.9348 (calculated: 233.9350).
Naphthalene-2-sulfonyl bromide (3e). Pale yellow solid
(0.30 g, 90%). 1H NMR (300 MHz, CDCl3): δ = 8.62 (s, 1H), 10 (a) W. Holly, G. R. Carlos, M. Isabel, A. L. Thompson and
8.10–7.99 (m, 4H), 7.80–7.70 (m, 2H); 13C NMR (75 MHz,
CDCl3): δ = 135.6, 132.1, 130.3, 130.1, 129.9, 128.3, 128.1, 121.0;
M. C. Willis, Org. Lett., 2011, 18, 4876–4878;
(b) G. M. B. Anthony, M. Takashi, P. Rina and T. Livio,
J. Org. Chem., 2003, 68, 8274–8276.
IR (neat): ν 3063, 2946, 1589, 1455, 1237, 1025, 840 cm−1
.
EI-MS: 270, 185, 149, 139, 123, 69, 57; EI-HRMS: exact mass 11 (a) J. Zhang, C. Wei and C. J. Li, Tetrahedron Lett., 2002, 43,
observed for C10H7ClO2S: 269.93500 (calculated: 269.93501).
Cyclohexanesulfonyl bromide (3f). Colorless oil (0.37 g,
95%). 1H NMR (300 MHz, CDCl3): δ = 3.54–3.44 (m, 1H),
2.40–2.36 (m, 2H), 1.97–1.94 (m, 2H), 1.73–1.60 (m, 3H),
1.45–1.12 (m, 3H); 13C NMR (75 MHz, CDCl3): δ = 74.7, 27.0,
24.8, 24.5; IR (neat): ν 2938, 2859, 1451, 1369, 1219, 1160, 751,
589 cm−1; EI-MS: m/z. 227, 225, 191, 163, 148, 111, 97, 83, 69,
55; EI-HRMS: exact mass observed for C6H11BrO2S: 225.9661
(calculated: 225.9663).
5731–5733; (b) J. Yuhong and R. S. Varma, Tetrahedron
Lett., 2005, 46, 6011–6014; (c) S. Shimizu, S. Shirakawa,
Y. Sasaki and C. Hirai, Angew. Chem., Int. Ed., 2000, 39,
1257–1259; (d) S. Kobashi and K. Manabe, Acc. Chem. Res.,
2002, 35, 209–217; (e) C. Junli, Acc. Chem. Res., 2002, 35,
533–538; (f) C. Wei and C. Jun Li, Green Chem., 2002, 4, 39–
41; (g) W. Wei and C. Jun Li, Chem. Commun., 2003, 1668–
1669; (h) C. Liang and C. Jun Li, Chem. Commun., 2004,
2362–2364; (i) C. J. Li, Chem. Rev., 2005, 105, 3095–3165;
( j) C. Wei and C. Jun Li, J. Am. Chem. Soc., 2003, 125, 9584–
9585; (k) O. Sijbren and B. F. N. E. Jan, J. Am. Chem. Soc.,
1999, 121, 6798–6806; (l) J. Yuhong and R. S. Varma, Org.
Lett., 2005, 7, 2409–2411; (m) X. Yao and C. Jun Li, Org.
Lett., 2005, 7, 4395–4398; (n) C. H. Helen, Org. Process Res.
Dev., 2007, 11, 114–120; (o) R. Breslow, Acc. Chem. Res.,
1991, 24, 159–164.
Acknowledgements
S.M. is thankful to CSIR, New Delhi for the financial support
through the XII five year plan project DITSF (code: CSC0204).
R.J. is thankful to CSIR, New Delhi for the financial support in
the form of a Senior Research Fellowship.
12 (a) S. E. Denmark, D. C. Forbes, D. S. Hays, J. S. DePue and
R. G. Wilde, J. Org. Chem., 1995, 60, 1393–1407; (b) H. Tian,
X. She and Y. Shi, Org. Lett., 2001, 3, 715–718;
(c) A. S. Cavallo and L. Bouerat, Org. Lett., 2000, 2, 3531–
3534; (d) H. Tian, X. She, J. Xu and Y. Shi, Org. Lett., 2001,
3, 1929–1931; (e) M. K. Wong, L. M. Ho, Y. S. Zheng, C. Yu
Ho and D. Yang, Org. Lett., 2001, 3, 2587–2590;
Notes and references
1 (a) T. W. Green and P. G. M. Wuts, Protective Groups in
Organic Synthesis, Wiley-Interscience, New York, 1999, vol.
3130 | Green Chem., 2014, 16, 3125–3131
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