ORDER
REPRINTS
Aryl Tosylate Synthesis Under Microwave Activation
Synthesis of Aryl Tosylates: General Procedure
1203
A dry 100 mL, single-necked, round-bottomed flask was charged with
10 mmol phenol, 100 mmol TsCl, and 200 mmol K CO . The reaction mix-
1
2
3
ture was irradiation for 3 min (or 5 min) at 250 W. After cooling to room tempe-
rature, the remaining mixture was dissolved in 50 mL of water and stirred for
several minutes. The pure product was easily obtained by filtration, wash with
a 0.1 N aqueous sodium hydroxide solution, water, and then dried in vacuo.
The yields as given below.
[
7]
Phenyl tosylate (2a). The general procedure gave 24.55 g (99% yield
1
based on TsCl) of white solid: m.p. 90–918C. H NMR (CDCl ): d 7.70
3
(
(
(
d, J ¼ 8.2 Hz, 2H), 7.31–3.25 (m, 5H), 7.01 (d, J ¼ 7.7 Hz, 2H), 2.42
s, 3H). GC-MS (IE, 70 eV) m/z (%) 91 (100), 155 (91), 65 (44), 248
2
1
14, Mþ), 63 (11), 51 (9), 92 (7), 89 (6). IR (KBr, cm ): 2909, 2859,
1
454, 1382, 1192, 865, 774, 725, 688, 656.
[
7]
4
-Methylphenyl tosylate (2b). The general procedure gave 25.68 g
1
(
(
(
98% yield) of white solid: m.p. 59–608C. H NMR (CDCl ): d 7.67
d, J ¼ 8.3 Hz, 2H), 7.29 (d, J ¼ 7.8 Hz, 2H), 7.03 (d, J ¼ 8.1 Hz, 2H), 6.83
3
d, J ¼ 8.5 Hz, 2H), 2.43 (s, 3H), 2.28 (s, 3H). GC-MS (IE, 70 eV) m/z (%)
9
1 (100), 155 (50), 65 (31), 77 (29), 107 (24), 262 (18, Mþ), 79 (14), 52
2
1
(
11). IR (KBr, cm ) 2928, 2854, 1593, 1505, 1461, 1378, 1197, 866, 782,
28, 692, 656.
-Methylphenyl tosylate (2c). The general procedure gave 25.68 g
7
[7]
2
1
(
98% yield) of white solid: m.p. 60–618C. H NMR (CDCl ): 7.71
3
(
d, J ¼ 8.4 Hz, 2H), 7.30 (d, J ¼ 8.1 Hz, 2H), 7.03–6.97 (m, 4H), 2.43
(
s, 3H), 2.06, (s, 3H). GC-MS (IE, 70 eV) m/z (%) 91 (100), 155 (46),
2
1
6
2
5 (28), 77 (24), 51 (19), 262 (14, Mþ), 101 (13), 52 (10). IR (KBr, cm ):
927, 2853, 1460, 1377, 1194, 873, 751, 660.
[
8]
1
-Naphtyl tosylate (2d). The general procedure gave 29 g (97% yield)
1
of white solid: m.p. 84–868C. H NMR (CDCl ): 7.92 (d, J ¼ 7.9 Hz, 1H),
3
7.82–7.73 (m, 4H), 7.51–7.35 (m, 3H), 7.29–7.21 (m, 3H), 2.40 (s, 3H).
GC-MS (IE, 70 eV) m/z (%) 115 (100), 143 (89), 91 (56), 65 (34), 298 (19,
2
1
Mþ), 89 (18), 155 (16), 63 (17), 144 (12), 116 (11). IR (KBr, cm ): 2926,
2
856, 1598, 1369, 1215, 1178, 890, 768, 711, 661.
[
1b,7]
2
,3,6-Trimethylphenyl tosylate (2e).
The general procedure gave
1
2
6.56 g (92% yield) of white solid: m.p. 58–608C. H NMR (CDCl ): 7.82
3
(
d, J ¼ 8.3 Hz, 1H), 7.34 (d, J ¼ 8.3 Hz, 2H), 6.95 (d, J ¼ 7.6 Hz, 2H), 2.46
(
s, 3H), 2.21 (s, 3H), 2.10 (s, 3H), 2.01 (s, 3H). GC-MS (IE, 70 eV) m/z (%)
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35 (100), 91 (70), 65 (24), 155 (19), 290 (14, Mþ), 79 (12), 136 (11), 77
2
1
9), 92 (8). IR (KBr, cm ): 2929, 2856, 1595, 1462, 1176, 892, 778, 731, 671.
(
[1b,7]
4-Nitrophenyl tosylate (2f).
The general procedure gave 28.81 g
1
(
98% yield) of white solid: m.p. 96–978C. H NMR (CDCl ): 8.19
3