JOURNAL OF CHEMICAL RESEARCH 2014 641
completion, 1 M NaOH (3 mL) was added and the reaction mixture
was diluted into ethyl acetate (100 mL). The organic layer was
extracted with 5% NaHCO3 (3 ×ꢀ50 mL), 0.1 M HCl (3×ꢀ50 mL), water
(25 mL), and brine (25 mL). The solvent was dried with sodium sulfate
and removed in vacuo.
2-Methoxyphenyl phenyl sulfone: White solid, m.p. 76–77 °C (lit.38
1
75 °C); H NMR (400 MHz, CDCl3): δ 7.38–7.55 (m, 5 H), 7.13–7.23
(m, 4 H), 3.81 (s, 3H); HRMS calcd for C13H12O3S: [M+] 248.0507;
found: 248.0506.
Received 6 August 2014; accepted 23 September 2014
Paper1402813 doi: 10.3184/174751914X14117977782502
Published online: 13 November 2014
Synthesis of sodium arylsulfinates; general procedure49
Sodium arylsulfinates were prepared by heating 2.5 g of sodium
sulfite (2.5 g), the appropriate ArSO2Cl (10 mmol) and sodium
hydrogen carbonate (1.68 g) in water (9.6 mL) at 70–80 °C for 4 h.
After cooling to room temperature, water was removed under vacuum
and the residue was extracted with ethanol.
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Synthesis of diphenyl sulfone derivatives; general procedure
A mixture of the sodium arylsulfinate (1 mmol), aryl tosylate
(1 mmol), [Cu(CH3CN)4]PF6 (0.1 mmol) and DMSO (2 mL) was stirred
at 120 °C under air for 6 h. Afterwards, water (2 mL) was added to the
reaction solution which was then filtered and the solution extracted by
Et2O (3×ꢀ2 mL). The organic phases were combined and evaporated
under reduced pressure. The residue was purified on a SiO2 column to
afford the desired product (eluent; ethyl acetate/hexane 1:15).
All products are known compounds and were characterised by their
1H NMR spectra and by HRMS.
Diphenyl sulfone: White solid, m.p. 125–127 °C (lit.37 125–126 °C);
1H NMR (400 MHz, CDCl3): δ 7.95 (d, J=7.2 Hz, 4H), 7.54 (t,
J=7.6 Hz, 2H), 7.50 (t, J=7.2 Hz, 4H); HRMS calcd for C12H10O2S:
[M+] 218.0402; found: 218.0403.
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4-Methoxyphenyl phenyl sulfone: Yellow solid, m.p. 91–92 °C
1
(lit.28 88–90 °C); H NMR (400 MHz, CDCl3): δ 7.85–7.95 (m, 4H),
7.47–7.54 (m, 3H), 6.93–6.99 (m, 2H), 3.85 (s, 3H); HRMS calcd for
C13H12O3S: [M+] 248.0507; found: 248.0506.
4-Methylphenyl phenyl sulfone: White solid, m.p.125–126 °C (lit.37
1
126–127 °C); H NMR (400 MHz, CDCl3): δ 7.94 (d, J=8.0 Hz, 2H),
10 T.M. Williams, T.M. Ciccarone, S.C. MacTough, C.S. Rooney, S.K.
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7.81 (d, J=7.6 Hz, 2H), 7.55 (t, J=7.6 Hz, 1H), 7.48 (t, J=7.6 Hz, 2H),
7.29 (d, J=8.0 Hz, 2H), 2.37 (s, 3H); HRMS calcd for C13H12O2S:
232.0558; found: 232.0559.
Methyl 4-(phenylsulfonyl)benzoate: Colourless oil37; 1H NMR
(400 MHz, CDCl3): δ 8.14 (d, J=7.6 Hz, 2H), 8.01 (d, J=7.6 Hz, 2H),
7.94 (d, J=7.6 Hz, 2H), 7.61 (d, J=6.8 Hz, 1H), 7.52 (m, 2 H), 3.94 (s,
3H); HRMS calcd for C14H12O4S: [M+] 276.0456; found: 276.0458.
4-Nitrophenyl phenyl sulfone: Yellow solid, m.p. 145–147 °C (lit.38
143–145 °C); 1H NMR (400 MHz, CDCl3): δ 8.27–8.37 (m, 2H),
8.07–8.16 (m, 2H), 7.92–8.01 (m, 2H), 7.58–7.66 (m, 1H), 7.51–7.60 (m,
2H); HRMS calcd for C12H9NO4S: [M+] 263.0252; found: 263.0251.
4-Trifluoromethylphenyl phenyl sulfone: Colourless solid, m.p.
1
89–91 °C (lit.38 90–91 °C); H NMR (400 MHz, CDCl3): δ 8.08 (d,
J=8.0 Hz, 2H), 7.90–8.02 (m, 2H), 7.81 (d, J=8.4 Hz, 2H), 7.50–7.64
(m, 3H); HRMS calcd for C13H9F3O2S: [M+] 286.0275; found: 286.0278.
4-Fluorophenyl phenyl sulfone: White solid, m.p. 103–105 °C (lit.37
105–107 °C); 1H NMR (400 MHz, CDCl3): δ 7.93–8.01 (m, 4H), 7.58 (t,
J=7.6 Hz, 1H), 7.50 (t, J=7.2 Hz, 2H), 7.14–7.22 (m, 2H); HRMS calcd
for C12H9FO2S: 236.0307: [M+] found: 236.0309.
2-Methylphenyl phenyl sulfone: White solid, m.p. 125–127 °C
1
(lit.38 125–127 °C); H NMR (400 MHz, CDCl3): δ 7.65–7.75 (m, 5H),
7.19–7.35 (m, 4 H), 3.33 (s, 3 H); HRMS calcd for C13H12O2S: [M+]
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5022.
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188.
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4719.
232.0558; found: 232.0556.
2-Fluorophenyl phenyl sulfone: White solid; (m.p. 93–95 °C
1
(lit.38 92–94 °C); H NMR (400 MHz, CDCl3): δ 7.40–7.52 (m, 5 H),
7.09–7.22 (m, 4 H); HRMS calcd for C12H9FO2S: [M+] 236.0307; found:
236.0310.
4-Acetylphenyl phenyl sulfone: Yellow solid, m.p. 131–133 °C (lit.28
132–134 °C); 1H NMR (400 MHz, CDCl3): δ 7.94–8.03 (m, 6H),
7.50–7.62 (m, 3H), 2.61 (s, 3H); HRMS calcd for C14H12O3S: [M+]
260.0507; found: 260.0504.
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