J. CHEM. RESEARCH (S), 1998 589
3m: mp 40±42 8C (lit.,16 42±43 8C); IR (KBr, ꢀ~max) 3080, 1750,
1600, 1330, 1280 and 1150 cm
3.90±4.48 (4 H, m) and 7.20±7.95 (5 H, m).
Experimental
Melting points were uncorrected. 1H NMR spectra were recorded
on a JEOL PMX 60 SI instrument in CDCl3 using SiMe4 as
1
; d 1.15 (3 H, t),
1H NMR
3n: mp 146±147 8C (lit.,17 146±146.5 8C); IR (KBr, ꢀ~max) 3065,
1595, 1320 and 1150 cm
(10 H, m).
internal standard, IR spectra on
photometer.
a Perkin-Elmer 683 spectro-
1
;
1H NMR d 4.25 (2 H, s) and 7.10±8.10
Metallic indium and other chemicals were from commercial
sources and used without puri®cation.
Received, 28th May 1998; Accepted, 3rd June 1998
Paper E/8/03996H
General Procedure for the Synthesis of Sulfones.ÐAromatic
sulfonyl chloride (1.0 mmol) and indium (1.5 mmol, small grains
cut from a bar of indium metal) were added to water (3 ml) and
then the appropriate alkyl bromide (1.5 mmol) was added. The
mixture was stirred at 0 8C for the time indicated in Table 1.
The product was extracted with ether (20 ml 2), and the extract
washed with brine. After being dried over anhydrous Na2SO4, the
solvent was evaporated under reduced pressure and the pure sulfone
was separated from the residue through preparative TLC (silica gel)
with cyclohexane±ethyl acetate as eluent.
References
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C. J. Li, Chem. Rev., 1993, 93, 2023; A. Lubineau, J. Auge and
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52, 5643.
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1931; L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc.,
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Organic Chemistry Series Vol. 10, ed. J. E. Baldwin and P. D.
Magnus, Pergamon, Oxford, 1993; S. Patai, Z. Rappoport and
C. Stirling, The Chemistry of Sulfones and Sulfoxides, Wiley,
New York, 1988.
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Part 1, ed. S. Patai, Wiley, New York, 1980, ch. 13; J. Smeek
and J. S. Fowler, J. Org. Chem., 1968, 33, 3422.
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Pharm. Bull., 1990, 38, 2357.
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11 J. Wildeman and A. M. Leusen, Synthesis, 1979, 733.
12 Beilstein, VI, 1923, p. 299.
3a: mp 51±52 8C (lit.,7 50±52 8C); IR (KBr, ꢀ~max) 3058, 1598,
1
1335, 1290 and 1150 cm
;
1H NMR d 2.42 (3 H, s), 3.69 (2 H, d,
J 6.4 Hz), 5.31±6.03 (3 H, m) and 7.21±7.88 (4 H, m).
3d: mp 116±118 8C (lit.,9 116±118 8C); IR (KBr, ꢀ~max) 3083, 1595,
1330, 1280 and 1145 cm
1
;
1H NMR d 2.40 (3 H, s), 4.21 (2 H,
d, J 6.3), 6.15±6.52 (1 H, m), 6.68 (1 H, d, J 15.8 Hz) and
7.05±7.88 (9 H, m).
3e: mp 109±110 8C (lit.,7 108±109.5 8C); IR (KBr, ꢀ~max) 3105,
1680, 1334, 1220 and 1139 cm
(2 H, s) and 7.23±8.03 (9 H, m)
1
;
1H NMR d 2.41 (3 H, s), 4.73
3f: mp 146±147 8C (lit.,10 145±147 8C); IR(KBr, ꢀ~max) 3093, 1690,
1320, 1280 and 1135 cm
and 7.20±8.00 (8 H, m).
1
;
1H NMR d 2.42 (3 H, s), 4.69 (2 H, s)
3g: mp 34±35 8C (lit.,11 34±35 8C); IR (KBr, ꢀ~max) 3090, 1750,
1600, 1330, 1280 and 1140 cm
1
;
1H NMR d 1.18 (3 H, t), 2.42
(3 H, s), 3.95±4.60 (4 H, m) and 7.25±7.90 (4 H, m).
3h: mp 144±145 8C (lit.,11 143±145 8C); IR (KBr, ꢀ~max) 3080,
1
1580, 1325, 1280 and 1140 cm
(2 H, s) and 7.00±7.60 (9 H, m).
;
1H NMR d 2.38 (3 H, s), 4.28
3i: Oil (lit.12); IR (®lm, ꢀ~max) 3090, 1600, 1325 and 1150 cm
1
;
1H NMR d 3.62 (2 H, d, J 6.4 Hz), 5.20±6.08 (3 H, m) and
7.19±7.90 (5 H, m).
3j: mp 109±110 8C (lit.,13 110 8C); IR (KBr, ꢀ~max) 3115, 1590,
1
;
1340 and 1135 cm
1H NMR d 4.22 (2 H, d, J 5.0), 6.20±6.58
(1 H, m), 6.68 (1 H, d, J 16.4 Hz) and 7.05±7.88 (10 H, m).
3k: mp 94±95 8C (lit.,14 93±95 8C); IR (KBr, ꢀ~max) 3100, 1690,
1340 and 1150 cm
m).
13 B. M. Trost and R. Braslau, J. Org. Chem., 1988, 53, 532.
14 J. Troger and O. Beck, J. Prakt. Chem., 1913, 87, 295.
15 R. T. Amel and P. T. Marek, J. Org. Chem., 1973, 38, 3513.
16 R. Otto, J. Prakt. Chem., 1884, 30, 343.
17 R. L. Shriner, H. C. Struck and W. J. Jorison, J. Am. Chem.
Soc., 1930, 52, 2069.
;
1H NMR d 4.72 (2 H, s) and 7.30±8.10 (10 H,
1
3l: mp 138±140 8C (lit.,15 138.5±139.5 8C); IR (KBr, ꢀ~max) 3100,
1700, 1340 and 1145 cm
(9 H, m).
;
1H NMR d 4.72 (2 H, s) and 7.23±8.00
1