2
674
K. Bahrami
LETTER
(4) (a) Monnee, M. C. F.; Marijne, M. F.; Brouwer, A. J.;
General
Melting points were determined in a capillary tube and are not cor-
Liskamp, R. M. J. Tetrahedron Lett. 2000, 41, 7991.
(b) Piatek, A.; Chapuis, C.; Jurczak, J. Helv. Chim. Acta
2002, 85, 1973. (c) Humljan, J.; Gobec, S. Tetrahedron Lett.
1
13
rected. H NMR and C NMR spectra were recorded on a Bruker-
00 spectrometer using TMS as internal standard.
2
2
005, 46, 4069.
General Procedure for the Preparation of Sulfonyl Chlorides
A mixture of sulfonic acid (1 mmol) and TAPC (0.3 mmol, 0.1 g)
was prepared in a mortar. The mixture was ground with a pestle for
(5) Kværnø, L.; Werder, M.; Hauser, H.; Carreira, E. M. Org.
Lett. 2005, 7, 1145.
(6) Meinzer, A.; Breckel, A.; Thaher, B. A.; Manicone, N.; Otto,
H.-H. Helv. Chim. Acta 2004, 87, 90.
1
min. Then, KCl (20 mol%, 0.015g) with a small drop of H O (by
2
a dropper) was added to the reaction mixture and grinding contin-
ued for 1 min (Table 2). The progress of the reaction was monitored
(7) Park, Y. J.; Shin, H. H.; Kim, Y. H. Chem. Lett. 1992, 1483.
(8) Schindler, W. Helv. Chim. Acta 1957, 40, 2148.
(9) Bossard, H. H.; Mory, R.; Schmid, M.; Zollinger, H. Helv.
Chim. Acta 1959, 42, 1653.
by TLC. After the completion of the reaction, H O (10 mL) was
2
added to the reaction mixture. The residue was then extracted with
EtOAc (4 × 5 mL), and the combined extracts were dried over
(10) Fujita, S. Synthesis 1982, 423.
(11) Barco, A.; Benetti, S.; Pollini, P.; Tadia, R. Synthesis 1974,
877.
MgSO . The filtrate was evaporated, and the corresponding sulfo-
4
nyl chloride was obtained as the only product.
(12) Blotny, G. Tetrahedron Lett. 2003, 44, 1499.
Spectral and Physical Data for Selected Compounds
Benzenesulfonyl Chloride (Table 2, Entry 1)
(13) (a) Schenk, R.; Römer, G. Ber. Dtsch. Chem. Ges. 1924, 57,
1343. (b) Allcock, H. R. J. Am. Chem. Soc. 1964, 86, 2591.
(c) Graham, J. C.; Marr, D. H. Can. J. Chem. 1972, 50,
3857. (d) Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y.
J. Org. Chem. 2008, 73, 2894. (e) Voznicova, R. K.;
Taraba, J.; Prihoda, J.; Alberti, M. Polyhedron 2008, 27,
2077. (f) Allcock, H. R.; Desorcie, J. L.; Harris, P. J. J. Am.
Chem. Soc. 1983, 105, 2814. (g) Rolland, O.; Griffe, L.;
Poupot, M.; Maraval, A.; Ouali, A.; Coppel, Y.; Fournie,
J. J.; Bacquet, G.; Turrin, C. O.; Caminade, A. M.; Majoral,
J. P.; Poupot, R. Chem. Eur. J. 2008, 14, 4836.
Oil (lit.15 oil). H NMR (200 MHz, CDCl ): d = 7.58–7.74 (m, 3 H),
1
3
1
3
7
1
.99–8.04 (m, 2 H). C NMR (50 MHz, CDCl ): d = 127.36,
3
30.26, 135.91, 144.64.
4
-Methoxybenzene-1-sulfonyl Chloride (Table 2, Entry 3)
16
1
Mp 38–40 °C (lit. mp 39–40 °C). H NMR (200 MHz, CDCl ):
3
d = 3.80 (s, 3 H), 7.07 (d, 2 H, J = 7.6 Hz), 7.90 (d, 2 H, J = 7.6 Hz).
1
3
C NMR (50 MHz, CDCl ): d = 55.62, 116.04, 129.73, 136.73,
3
1
67.50.
(
14) (a) Bahrami, K.; Khodaei, M. M.; Kavianinia, I. Synthesis
2007, 547. (b) Bahrami, K.; Khodaei, M. M.; Naali, F. J.
Org. Chem. 2008, 73, 6835. (c) Bahrami, K.; Khodaei, M.
M.; Tirandaz, Y. Synthesis 2009, 369. (d) Khodaei, M. M.;
Bahrami, K.; Tirandaz, Y. J. Sulfur Chem. 2009, 30, 581.
4
-Nitrobenzene-1-sulfonyl Chloride (Table 2, Entry 6)
15
1
Mp 71–73 °C (lit. mp 72–73 °C). H NMR (200 MHz, CDCl ):
d = 8.26 (d, 2 H, J = 8.0 Hz), 8.48 (d, 2 H, J = 8.0 Hz). C NMR (50
MHz, CDCl ): d = 125.48, 128.96, 149.02, 151.72.
3
1
3
3
(e) Bahrami, K.; Khodaei, M. M.; Farrokhi, A. Tetrahedron
Cyclohexanesulfonyl Chloride (Table 2, Entry 11)
2009, 65, 7658. (f) Bahrami, K.; Khodaei, M. M.;
Oil (lit.15 oil). H NMR (200 MHz, CDCl ): d = 1.22–1.39 (m, 3 H),
1
Soheilizad, M. Synlett 2009, 2773. (g) Bahrami, K.;
Khodaei, M. M.; Soheilizad, M. J. Org. Chem. 2009, 74,
9287. (h) Bahrami, K. Tetrahedron Lett. 2006, 47, 2009.
(i) Khodaei, M. M.; Bahrami, K.; Khedri, M. Can. J. Chem.
3
1
3
7
.55–1.73 (m, 3 H), 1.90–1.96 (m, 2 H), 2.31–2.38 (m, 2 H), 3.45–
.56 (m, 1 H). 13C NMR (50 MHz, CDCl ): d = 25.10, 25.36, 27.62,
3
5.29.
2007, 85, 7. (j) Khodaei, M. M.; Bahrami, K.; Karimi, A.
Synthesis 2008, 1682. (k) Bahrami, K.; Khodaei, M. M.;
Karimi, A. Synthesis 2008, 2543. (l) Bahrami, K.; Khodaei,
M. M.; Naali, F. Synlett 2009, 569. (m) Khodaei, M. M.;
Bahrami, K.; Sheikh Arabi, M. J. Sulfur Chem. 2010, 31,
Acknowledgment
We are thankful to the Razi University Research Council for partial
support of this work.
83. (n) Bahrami, K.; Khodaei, M. M.; Sheikh Arabi, M.
Tetrahedron Lett. 2010, 51, 6939. (o) Bahrami, K.;
Khodaei, M. M.; Soheilizad, M. Tetrahedron Lett. 2010, 51,
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Synlett 2011, No. 18, 2671–2674 © Thieme Stuttgart · New York