H. Wang, L. Jiang, T. Chen, Y. Li
) ppm. 13C NMR (100 MHz, CDCl
): δ = 146.4, 139.6, 136.1,
FULL PAPER
CAS: 14065-22-6. H NMR (400 MHz, CDCl
1
3
): δ = 7.36–7.21 (m,
NH
2
3
6
H, Ar-H), 7.08 (d, J = 8.0 Hz, 1 H, Ar-H), 6.88 (m, 2 H, 1-H,
Ar-H), 3.87 (s, 6 H, OCH ): δ
) ppm. 13C NMR (100 MHz, CDCl
157.6, 134.8, 131.9, 131.6, 129.3, 128.5, 127.2, 124.3, 121.4, 111.1,
129.0, 127.6, 125.5, 121.3, 116.4 ppm. GC–MS (EI): m/z = 201
[M] .
+
3
3
=
4-(Phenylsulfanyl)Phenol (2p): The product was obtained (ethyl ace-
+
56.1 ppm. GC–MS (EI): m/z = 216 [M] .
tate/petroleum ether, 1:20) as a colorless oil in 30% yield. CAS:
1
4-Bromophenyl Phenyl Thioether (2h): The product was obtained
5633-55-6. H NMR (400 MHz, CDCl
3
): δ = 7.36 (d, J = 8.8 Hz,
(
6
petroleum ether) as a colorless oil in 89% yield. CAS: 65662-88-
2 H, Ar-H), 7.24–7.13 (m, 5 H, Ar-H), 6.83 (d, J = 8.8 Hz, 2 H,
1
13
. H NMR (400 MHz, CDCl
3 3
): δ = 7.39 (d, J = 8.4 Hz, 2 H, Ar- Ar-H), 5.86 (br. s, 1 H, OH) ppm. C NMR (100 MHz, CDCl ):
H), 7.36–7.24 (m, 5 H, Ar-H), 7.16 (d, J = 8.4 Hz, 2 H, 2-H) ppm.
δ = 156.1, 138.6, 135.7, 129.1, 128.5, 126.0, 124.7, 116.7 ppm. GC–
13
+
C NMR (100 MHz, CDCl
3
): δ = 135.7, 135.0, 132.4, 132.3, 131.7, MS (EI): m/z = 202 [M] .
+
1
2
29.5, 127.7, 121.0 ppm. GC–MS (EI): m/z = 264 [M] , 266 [M +
4-Nitrophenyl Phenyl Thioether (2q): The product was obtained
+
] .
(
ethyl acetate/petroleum ether, 1:20) as a yellow solid in 58% yield
1
2-Bromophenyl Phenyl Thioether (2i): The product was obtained
(90 °C, 18 h) or in 73% yield (110 °C, 24 h). CAS: 952-97-6.
NMR (400 MHz, CDCl ): δ = 8.06 (d, J = 9.2 Hz, 2 H, Ar-H),
7.56–7.54 (m, 2 H, Ar-H), 7.47–7.45 (m, 3 H, Ar-H), 7.18 (d, J =
H
(
1
petroleum ether) as a slightly yellow solid in 89% yield. CAS:
3
1
5861-48-0. H NMR (400 MHz, CDCl
3
): δ = 7.55 (d, J = 8.0 Hz,
1
3
1
H, Ar-H), 7.46–7.37 (m, 5 H, Ar-H), 7.13 (t, J = 7.6 Hz, 1 H,
3
9.2 Hz, 2 H, Ar-H) ppm. C NMR (100 MHz, CDCl ): δ = 148.7,
Ar-H), 7.02 (t, J = 7.6 Hz, 1 H, Ar-H), 6.92 (d, J = 8.0 Hz, 1 H,
Ar-H) ppm. 13C NMR (100 MHz, CDCl
): δ = 138.9, 133.7, 133.2,
33.0, 129.9, 129.8, 128.6, 128.0, 127.4, 123.1 ppm. GC–MS (EI):
145.5, 134.9, 130.5, 130.2, 129.9, 126.8, 124.2 ppm. GC–MS (EI):
m/z = 231 [M] .
+
3
1
Di-p-tolylsulfane (3a): The product was obtained (petroleum ether)
+
+
m/z = 264 [M] , 266 [M + 2] .
-Chlorophenyl Phenyl Thioether (2j): The product was obtained
petroleum ether) as a colorless oil in 88% yield. CAS: 13343-26-
1
as a white solid in 89% yield. CAS: 620-94-0. H NMR (400 MHz,
4
CDCl
3
): δ = 7.20 (d, J = 8.0 Hz, 4 H, Ar-H), 7.07 (d, J = 8.0 Hz,
1
3
(
5
4 H, Ar-H), 2.29 (s, 6 H, CH ) ppm. C NMR (100 MHz, CDCl ):
3
3
1
.
H NMR (400 MHz, CDCl
3
): δ = 7.35–7.25 (m, 9 H, Ar-
H) ppm. C NMR (100 MHz, CDCl ): δ = 135.3, 134.8, 133.2,
32.2, 131.5, 129.49, 129.48, 127.6 ppm. GC–MS (EI): m/z = 220
δ = 137.1, 132.8, 131.2, 130.1, 21.2 ppm. GC–MS (EI): m/z = 214
13
+
3
[M] .
1
(
4-Bromophenyl)(p-tolyl)sulfane (3b): The product was obtained
+
+
[
M] , 222 [M + 2] .
(
petroleum ether) as a white solid in 89% yield. CAS: 22865-54-9.
1
(
2-Chlorophenyl)(phenyl)sulfane(2k): The product was obtained (pe-
H NMR (400 MHz, CDCl
3
): δ = 7.36 (d, J = 8.4 Hz, 2 H, Ar-H),
1
troleum ether) as a colorless oil in 93% yield. CAS: 33667-82-2. H
NMR (400 MHz, CDCl ): δ = 7.44 (d, J = 8.0 Hz, 2 H, Ar-H), 7.09 (d, J = 8.8 Hz, 2 H, Ar-H), 2.35 (s, 3 H, CH
.37–7.32 (m, 4 H, Ar-H), 7.14–7.08 (m, 2 H, Ar-H), 6.98 (d, J = (100 MHz, CDCl ): δ = 138.3, 137.0, 132.8, 132.2, 131.1, 130.7,
7.30 (d, J = 8.4 Hz, 2 H, Ar-H), 7.15 (d, J = 8.0 Hz, 2 H, Ar-H),
1
3
3
3
) ppm. C NMR
7
8
1
3
13
+
.0 Hz, 1 H, Ar-H) ppm. C NMR (100 MHz, CDCl
3
): δ = 136.5,
130.4, 120.3, 21.3 ppm. GC–MS (EI): m/z = 278 [M] , 280 [M +
+
33.4, 133.1, 132.9, 130.3, 129.8, 129.6, 128.2, 127.3, 127.2 ppm.
2] .
+
+
GC–MS (EI): m/z = 220 [M] , 222 [M + 2] .
-(Phenylthio)benzonitrile (2l): The product was obtained (ethyl
acetate/petroleum ether, 1:20) as a colorless oil in 94% yield. CAS:
(
4-Chlorophenyl)(p-tolyl)sulfane (3c): The product was obtained
4
(petroleum ether) as a white solid in 92% yield. CAS: 22865-55-0.
1
H NMR (400 MHz, CDCl
3
): δ = 7.29 (d, J = 8.0 Hz, 2 H, Ar-H),
1
5
1238-46-1. H NMR (400 MHz, CDCl
Ar-H), 7.16 (d, J = 8.0 Hz, 2 H, Ar-H) ppm. C NMR (100 MHz,
CDCl ): δ = 145.9, 134.6, 132.5, 131.0, 130.1, 129.5, 127.5, 118.9,
08.9 ppm. GC–MS (EI): m/z = 211 [M] .
3
): δ = 7.52–7.41 (m, 7 H, 7.22 (d, J = 8.8 Hz, 2 H, Ar-H), 7.18–7.14 (m, 4 H, 3-H, 1-H), 2.35
13
13
(s, 3 H, CH
3 3
) ppm. C NMR (100 MHz, CDCl ): δ = 138.2, 136.2,
3
132.7, 132.5, 131.1, 131.0, 130.4, 129.3, 21.3 ppm. GC–MS (EI):
+
+
+
1
m/z = 234 [M] , 236 [M + 2] .
Ethyl 4-(Phenylthio)benzoate (2m): The product was obtained
CH Cl /petroleum ether, 1:10) as a colorless oil in 92% yield.
CAS: 10129-07-4. H NMR (400 MHz, CDCl
8
3
o-Tolyl(p-tolyl)sulfane (3d): The product was obtained (petroleum
ether) as a colorless liquid in 96% yield. CAS: 4279-70-3. H NMR
1
(
2
2
1
3
): δ = 7.90 (d, J =
.8 Hz, 2 H, Ar-H), 7.47 (d, J = 9.2 Hz, 2 H, Ar-H), 7.38–7.36 (m,
H, Ar-H), 7.20 (d, J = 8.8 Hz, 2 H, Ar-H), 4.37 (q, J = 7.6 Hz, 2
), 1.36 (t, J = 7.6 Hz, 3 H, CH
) ppm. 13C NMR (100 MHz, 21.2, 20.6 ppm. GC–MS (EI): m/z = 214 [M] .
): δ = 166.3, 144.2, 133.7, 132.9, 130.2, 129.7, 128.7, 128.2,
(400 MHz, CDCl
CH ), 2.31 (s, 3 H, CH
139.0, 137.0, 135.4, 131.9, 131.7, 131.2, 130.6, 130.2, 127.3, 126.7,
3
): δ = 7.20–7.06 (m, 8 H, Ar-H), 2.37 (s, 3 H,
1
3
3
3 3
) ppm. C NMR (100 MHz, CDCl ): δ =
+
H, CH
CDCl
2
3
3
4-(p-Tolylthio)phenol (3e): The product was obtained (ethyl acetate/
+
128.0, 61.1, 14.5 ppm. GC–MS (EI): m/z = 258 [M] .
petroleum ether, 1:20) as a white solid in 32% yield. CAS: 5633-
1
1
-Naphyl Phenyl Thioether (2n): The product was obtained (petro-
56-7. H NMR (400 MHz, CDCl
Ar-H), 7.14 (d, J = 8.0 Hz, 2 H, Ar-H), 7.06 (d, J = 8.0 Hz, 2 H,
): δ = 8.39–8.36 (m, 1 H, Ar-H), 7.85–7.83 Ar-H), 6.78 (d, J = 8.8 Hz, 2 H, Ar-H), 4.96 (br. s, 1 H, OH), 2.30
3
): δ = 7.30 (d, J = 8.4 Hz, 2 H,
1
leum ether) as a colorless oil in 88% yield. CAS: 7570-98-1.
NMR (400 MHz, CDCl
m, 2 H, Ar-H), 7.65 (d, J = 7.2 Hz, 1 H, Ar-H), 7.51–7.49 (m, 2
H, Ar-H), 7.41 (t, J = 7.2 Hz, 1 H, Ar-H), 7.22–7.14 (m, 5 H, Ar-
H) ppm. 13C NMR (100 MHz, CDCl
): δ = 137.1, 134.4, 133.8,
32.7, 131.4, 129.4, 129.2, 129.1, 128.7, 127.1, 126.6, 126.3, 126.0,
H
3
1
3
(
3 3
(s, 3 H, CH ) ppm. C NMR (100 MHz, CDCl ): δ = 155.6, 136.5,
134.6, 134.3, 130.0, 129.8, 126.3, 116.5, 21.1 ppm. GC–MS (EI):
+
3
m/z = 216 [M] .
1
1
N-[4-(p-Tolylthio)phenyl]acetamide (3f): The product was obtained
+
25.8 ppm. GC–MS (EI): m/z = 236 [M] .
(
ethyl acetate/petroleum ether, 3:2) as a white solid in 82% yield.
1
4
-Aminophenyl Phenyl Thioether (2o): The product was obtained
H NMR (400 MHz, CDCl
7.33 (br. s, 1 H, NH), 7.27 (m, 2 H, Ar-H), 7.22 (d, J = 8.4 Hz, 2
H, Ar-H), 7.10 (d, J = 8.0 Hz, 2 H, Ar-H), 2.32 (s, 3 H, CH ), 2.16
): δ = 168.4, 137.3,
H, Ar-H), 6.69 (d, J = 8.4 Hz, 2 H, Ar-H), 3.87 (br. s, 2 H, 137.1, 132.5, 131.9, 131.6, 131.3, 130.1, 120.7, 24.7, 21.2 ppm. GC–
3
): δ = 7.43 (d, J = 8.4 Hz, 2 H, Ar-H),
(ethyl acetate/petroleum ether, 1:3) as a pale solid in 87% yield.
1
CAS: 1135-14-4. H NMR (400 MHz, CDCl
8
3
3
): δ = 7.31 (d, J =
3
1
3
.4 Hz, 2 H, Ar-H), 7.22 (t, J = 7.2 Hz, 2 H, Ar-H), 7.14–7.08 (m, (s, 3 H, CH ) ppm. C NMR (100 MHz, CDCl
3
3
2328
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Eur. J. Org. Chem. 2010, 2324–2329