JOURNAL OF CHEMICAL RESEARCH 2014 449
Typical procedure
2-Fluorophenyl phenyl sulfone: White solid;, m.p. 93–96 °C
16
1
(
7
2
lit. 92–94 °C); H NMR (400 MHz, CDCl ): δ 7.40–7.51 (m, 5 H),
A mixture of the sodium aryl bromides (1 mmol), sodium arylsulfinate
3
.09–7.20 (m, 4 H); HRMS calcd for C H FO S: 236.0307, found:
(1.2 mmol), CuBr (0.1 mmol), pyridine (0.15 mmol) and DMI solvent
12
9
2
36.0309.
-Naphthyl phenyl sulfone: Colourless solid, m.p. 119–120 °C (lit.
(
2 mL) was stirred at 80 °C under air for 12 h. Afterwards, water (2 mL)
16
2
was added to the reaction solution which was then filtered through a
filter paper. The solution extracted by Et O (2 mL) three times. The
organic phase was combined and evaporated under reduced pressure.
The residue was purified on a SiO column to afford the desired product
1
1
(
19–121 °C); H NMR (400 MHz, CDCl ): δ 8.58 (s, 1H), 7.95–8.06
3
2
m, 3H), 7.93 (d, J=8.8 Hz, 1H), 7.82–7.89 (m, 2H),7.48–7.66 (m, 5H);
HRMS calcd for C H O S: 268.0558, found: 268.0556.
16
12
2
2
by ethyl acetate/hexane (1:12).
Received 18 April 2014; accepted 8 June 2014
Paper 1402592 doi: 10.3184/174751914X14034421692005
Published online: 12 July 2014
All products are known compounds and were characterised by
1
melting point, H NMR and HRMS.
The products characterised were prepared using HMPA (hexamethyl
phosphoramide) as solvent. However, due to the high reported
carcinogenecity and mutagenicity of this solvent, its use was curtailed.
References
2
2
Diphenyl sulfone: White solid, m.p. 126–127 °C (lit. 125–126 °C);
1
2
3
4
5
S. Patai, Z. Rappoport and C.J.M. Stirling, eds, The chemistry of sulfones
and sulfoxides. Wiley, New York, 1988.
N.S. Simpkins, Sulfones in organic synthesis. Pergamon Press, Oxford,
1
H NMR (400 MHz, CDCl ): δ 7.94 (d, J=7.6 Hz, 4H), 7.55 (t,
3
J=7.6 Hz, 2H), 7.50 (t, J=7.6 Hz, 4H); HRMS calcd for C H O S:
1
2
10
2
1993.
218.0402, found: 218.0405.
Z.-Y. Sun, E. Botros, A.-D. Su, Y. Kim, E. Wang, N.Z. Baturay and C.-H.
Kwon, J. Med. Chem., 2000, 43, 4160.
2
3
4
-Methoxyphenyl phenyl sulfone: Yellow solid, m.p. 90–92 °C (lit.
1
8
6
2
8–90 °C); H NMR (300 MHz, CDCl3) δ 7.90 (m, 4H), 7.51 (m, 3H),
T. Otzen, E.G. Wempe, B. Kunz, R. Bartels, G. Lehwark-Yvetot, W.
Hänsel, K.J. Schaper and J.K. Seydel, J. Med. Chem., 2004, 47, 240.
R.A. Hartz, A.G. Arvanitis, C. Arnold, J.P. Rescinito, K.L. Hung, G.
Zhang, H. Wong, D.R. Langley, P.J. Gilligan and G.L. Trainor, Bioorg.
Med. Chem. Lett., 2006, 16, 934.
.96 (m, 2H), 3.84 (s, 3H); HRMS calcd for C H O S: 248.0507, found:
1
3
12
3
48.0509.
-Methylphenyl phenyl sulfone: White solid, m.p. 125–127 °C (lit.
2
2
4
1
126–127 °C); H NMR (400 MHz, CDCl ): δ 7.92 (d, J=8.0 Hz, 2H),
3
6
7
8
9
Á. Molnár, ed. Palladium-catalysed coupling reactions practical aspects
and future developments. Wiley, Weinheim, 2013.
A. de Meijere, S. Bräse and M. Oestreich, eds, Metal-catalysed cross-
coupling reactions and more. Wiley, Weinheim, 2014.
7.81 (d, J=8.0 Hz, 2H), 7.54 (t, J=7.6 Hz, 1H), 7.49 (t, J=7.6 Hz,
2
2
H), 7.30 (d, J=8.0 Hz, 2H), 2.37 (s, 3H); HRMS calcd for C H O S:
1
3
12
2
32.0558, found: 232.0557.
-Nitrophenyl phenyl sulfone: Yellow solid, m.p. 145–149 °C (lit.
1
6
S. Cacchi, G. Fabrisi, A. Goggiamani and L.M. Parisi, Org. Lett., 2002, 4,
4
4719.
1
143–145 °C); H NMR (400 MHz, CDCl ): δ 8.27–8.38 (m, 2H),
3
J.M. Baskin and Z. Wang, Org. Lett., 2002, 4, 4423.
8
2
.07–8.15 (m, 2H), 7.92–8.00 (m, 2H), 7.58–7.66 (m, 1H), 7.51–7.61 (m,
10
S. Cacchi, G. Fabrisi, A. Goggiamani, L.M. Parisi, Synlett, 2003, 361.
H); HRMS calcd for C H NO S: 263.0252, found: 263.0250.
11 S. Cacchi, G. Fabrisi, A. Goggiamani, L.M. Parisi and R. Bernini, J. Org.
Chem., 2004, 69, 5608.
12 T. Zhou and Z.-C. Chen, J. Chem. Res. (S), 2000, 474.
12
9
4
4
-Trifluoromethylphenyl phenyl sulfone: Colourless solid, m.p.
16
1
8
9–90 °C (lit. 90–91 °C); H NMR (400 MHz, CDCl ): δ 8.07 (d,
3
13
F.-Y. Wang, Z.-C. Chen and Q.-G. Zheng, J. Chem. Res. (S), 2003, 620.
J=8.0 Hz, 2H), 7.90–8.03 (m, 2H), 7.80 (d, J=8.8 Hz, 2H), 7.50–7.65
m, 3H); HRMS calcd for C H F O S: 286.0275, found: 286.0276.
14 N. Umierski and G. Manolikakes, Org. Lett., 2013, 15, 188.
(
13
9
3
2
15 D. Kumar, V. Arun, M. Pilania and K.P.C. Shekar, Synlett, 2013, 24, 831.
16 B.P. Bandgar, S.V. Bettigeri and J. Phopase, Org. Lett., 2004, 6, 2105.
17 V. Garzya, I.T. Forbes, S. Lauru and P. Maragni, Tetrahedron Lett., 2004,
2
2
4
-Fluorophenyl phenyl sulfone: White solid, m.p. 103–104 °C (lit.
1
1
05–107 °C); H NMR (400 MHz, CDCl ): δ 7.96 (m, 4H), 7.57 (t,
3
4
5, 1499.
J=7.6 Hz, 1H), 7.50 (t, J=7.6 Hz, 2H), 7.18 (m, 2H); HRMS calcd for
18
A. Kar, I.A. Sayyed, W.F. Lo, H.M. Kaiser, M. Beller and M.K. Tse. Org.
Lett., 2007, 9, 3405.
C H FO S: 236.0307, found: 236.0305.
12
9
2
1
6
2
-Methoxyphenyl phenyl sulfone: White solid, m.p. 75–77 °C (lit.
19
F. Huang and R.A. Batey, Tetrahedron, 2007, 63, 7667.
1
7
5 °C); H NMR (400 MHz, CDCl ): δ 7.38–7.57 (m, 5 H), 7.12–7.23
20 K.M. Lakshmi, B. Neelima, B. Sreedhar and R. Chakravarti, Synlett,
3
(
2
s, 4 H), 3.80 (s, 3H); HRMS calcd for C H O S: 248.0507, found:
2008, 1455.
13
12
3
2
1
K. Bahrami, M.M. Khodei and F. Shahbazi. Tetrahedron Lett., 2008, 49,
931.
2 H. Yang, Y. Li, M. Jiang, J. Wang and H. Fu, Chem. Eur. J., 2011, 17, 5652.
48.0511.
-Methylphenyl phenyl sulfone: White solid, m.p. 125–126 °C
3
2
2
16
1
(
7
lit. 125–127 °C); H NMR (400 MHz, CDCl ): δ 7.65–7.76 (m, 5H),
3
23 W. Zhu and D. Ma, J. Org. Chem., 2005, 70, 2696.
24 Y. Yuan and S. Guo. Synlett, 2011, 18, 2750.
25 Y. Peng. J. Chem. Res., 2014, 38, 265.
.19–7.36 (m, 4 H), 3.32 (s, 3 H); HRMS calcd for C H O S: 232.0558,
13
12
2
found: 232.0553.
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