98 J. Chin. Chem. Soc., Vol. 58, No. 1, 2011
Tan et al.
6H, ArH), 7.17-7.23 (m, 3H, ArH), 2.31 (s, 3H, CH3). 13
C
EA 1:1). 1H NMR (400 MHz, acetone-d6) d 7.44 (dd, J =
6.6, 2.0 Hz, 2H, ArH), 7.29-7.35 (m, 4H, ArH), 7.06 (dd, J
= 6.6, 2.0 Hz, 2H, ArH), 2.33 (s, 3H, CH3). 13C NMR (100
MHz, acetone-d6) d 141.3, 137.0, 134.7, 133.1, 133.0,
131.8, 131.3, 129.7, 127.9, 120.4, 20.7. MS (ESI) m/z: 278.
Anal. Calcd. For C13H11BrS: C, 55.92; H, 3.97. Found: C,
55.78; H, 3.76.
NMR (100 MHz, acetone-d6) d 138.6, 137.8, 133.0, 132.0,
130.9, 130.5, 130.0, 127.4, 21.1. 1H and 13C NMR spectra
are consistent with the literature.28
4-Acetylphenyl phenyl sulfide
A white solid. The product was purified by column
chromatography (Hex/EA 8:1). Rf = 0.55 (Hex/EA 1:1).
Mp = 67 °C (lit.19 Mp = 66-67°C ). 1H NMR (400 MHz, ac-
etone-d6) d 7.89 (dd, J = 6.7, 1.9 Hz, 2H, ArH), 7.45-7.53
(m, 5H, ArH), 7.26 (dd, J = 6.7, 1.9 Hz, 2H, ArH), 2.53 (s,
3H, CH3). 13C NMR (100 MHz, acetone-d6) d 196.8, 144.8,
135.8, 134.4, 133.0, 130.7, 129.7, 129.6, 128.4, 26.5.
2-Phenylsulfanylbenzenesulfonamide
4-Bromophenyl 4-tolyl sulfide
A pale orange solid. The product was purified by col-
umn chromatography (Hex/EA 20:1). Rf = 0.55 (Hex/EA
1
1:1). Mp = 83 °C (lit.43 Mp = 83-84 °C). H NMR (400
MHz, acetone-d6) d 7.74 (dd, J = 6.6, 2.0 Hz, 2H, ArH),
7.33 (d, J = 8.0 Hz, 2H, ArH), 7.23 (d, J = 8.0 Hz, 2H,
ArH), 7.15 (dd, J = 6.6, 2.0 Hz, 2H, ArH), 2.34 (s, 3H,
CH3). 13C NMR (100 MHz, acetone-d6) d 139.3, 137.9,
133.6, 132.9, 131.6, 131.2, 130.8, 120.5, 21.0.
A white solid. The product was purified by column
chromatography (Hex/EA 2:1). Rf = 0.3 (Hex/EA 1:1). Mp
= 111 °C (lit.38 Mp = 111-113 °C). 1H NMR (400 MHz, ace-
tone-d6) d 8.0 (dd, J = 7.6, 1.2 Hz, 1H, ArH), 7.50-7.53 (m,
2H, ArH), 7.40-7.47 (m, 4H, ArH), 7.30-7.37 (m, 1H, ArH),
7.13 (dd, J = 7.6, 1.2 Hz, 1H, ArH), 6.68 (s, 2H, SO2NH2).
13C NMR (100 MHz, acetone-d6) d 142.4, 137.4, 134.4,
134.1, 132.9, 131.9, 130.4, 129.4, 128.7, 126.8.
2-(4-Bromophenylsulfanyl)benzenesulfona-mide
A light yellow solid. The product was purified by col-
umn chromatography (Hex/EA 3:1). Rf = 0.34 (Hex/EA
1:1). Mp = 117-119 °C. 1H NMR (400 MHz, acetone-d6) d
8.01-8.04 (m, 1H, ArH), 7.58-7.60 (m, 2H, ArH), 7.38-
7.46 (m, 4H, ArH), 7.21-7.22 (m, 1H, ArH), 6.67 (bs, 2H,
SO2NH2). 13C NMR (100 MHz, acetone-d6) d 142.6, 135.9,
135.3, 133.9, 133.0, 132.9, 132.4, 128.5, 127.1, 122.7. MS
(ESI) m/z: 345, 343. Anal. Calcd. For C12H10BrNO2S2: C,
41.87; H, 2.93; N, 4.07. Found: C, 41.57; H, 2.86; N, 3.95.
(2-Aminosulfonyl-4-nitro)phenyl 3,4-dimethoxyphenyl
sulfide
4-Nitrophenyl phenyl sulfide
A slightly yellow solid. The product was purified by
column chromatography (Hex/EA 5:1). Rf = 0.42 (Hex/EA
1:1). Mp = 53-54°C (lit.39 Mp = 52.5-53°C). 1H NMR (400
MHz, CDCl3) d 8.04 (dd, J = 7.3, 1.8 Hz, 2H, ArH), 7.54-
7.50 (m, 2H, ArH), 7.45-7.42 (m, 3H, ArH), 7.16 (d, J = 8.0
Hz, 2H, ArH). 13C NMR (100 MHz, CDCl3) d 148.4, 145.4,
134.7, 130.5, 130.0, 129.6, 126.7, 124.0.
A yellow solid. The product was purified by column
chromatography (Hex/EA 1:1). Rf = 0.2 (Hex/EA 1:1). Mp:
216 °C; 1H NMR (400 MHz, acetone-d6) d 8.70 (d, J = 2.6
Hz, 2H, ArH), 8.18 (dd, J = 8.8, 2.6 Hz, 1H, ArH), 7.23 (dd,
J = 8.2, 2.1 Hz, 1H, ArH), 7.13-7.18 (m, 3H, ArH), 6.97
(bs, 2H, SO2NH2), 3.90 (s, 3H, CH3), 3.83 (s, 3H, CH3). 13C
NMR (100 MHz, acetone-d6) d 152.5, 151.4, 149.4, 145.2,
140.5, 129.9, 129.5, 126.8, 123.9, 120.4, 119.2, 113.7, 56.2,
56.1. MS (ESI) m/z: 370. Anal. Calcd. For C14H14N2O6S2:
C, 45.40; H, 3.81; N, 7.56. Found: C, 45.37; H, 3.53; N,
7.48.
4-Fluorophenyl phenyl sulfide
A slight yellow liquid. The product was purified by
column chromatography (Hex/EA 10:1). Rf = 0.58 (Hex/
1
EA 1:1). Bp = 136 °C (lit.40 Bp = 133-135 °C). H NMR
(400 MHz, CDCl3) d 7.40-7.44 (m, 4H, ArH), 6.97-7.01
(m, 5H, ArH). 13C NMR (100 MHz, CDCl3) d 163.8, 161.3,
132.1, 131.3, 131.2, 128.2, 116.4, 116.2.
4-Chlorophenyl phenyl sulfide
A white solid. The product was purified by column
chromatography (Hex/EA 10:1). Rf = 0.6 (Hex/EA 1:1).
Mp = 62-64 °C. 1H NMR (400 MHz, CDCl3) d 7.38-7.41
(m, 4H, ArH), 7.25-7.28 (m, 5H, ArH). 13C NMR (100
MHz, CDCl3) d 135.07, 133.58, 129.27, 129.26, 128.19,
128.15, 127.53, 127.48. MS (ESI) m/z: 222, 220 (lit.41 m/z
for M+ 222, 220).
4-Chlorophenyl 4-nitrophenyl sulfide
A light yellow solid. The product was purified by col-
umn chromatography (Hex/EA 20:1). Rf = 0.55 (Hex/EA
1:1). Mp: 87-88 °C (lit.44 Mp = 87 °C). 1H NMR (400 MHz,
acetone-d6) d 8.14 (d, J = 8.8 Hz, 2H, ArH), 7.59 (d, J = 8.8
Hz, 2H, ArH), 7.54 (d, J = 8.4 Hz, 2H, ArH), 7.35 (d, J =
8.8 Hz, 2H, ArH). 13C NMR (100 MHz, acetone-d6) d
147.8, 136.7, 136.1, 131.0, 130.4, 130.1, 128.1, 124.9.
4-Bromophenyl 2-tolyl sulfide
Alightly yellow liquid.42 The product was purified by
column chromatography (Hex/EA 10:1). Rf = 0.52 (Hex/