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2. Conclusions
275.
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54, 9791.
9. Sengupta, S.; Sarma, D. S.; Mondal, S. Tetrahedron:
Asymmetry 2001, 12, 513.
We have described an efficient synthesis of various
a-iodo b-ketosulfones and a-iodo methylsulfones, by
the reaction of b-ketosulfones with iodine monochloride
as an iodine source, followed by a base-induced
cleavage.
10. Sengupta, S.; Sarma, D. S.; Mondal, S. Tetrahedron:
Asymmetry 1998, 9, 2311.
2.1. Synthesis of a-iodo b-ketosulfones
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Romero, A. J. Org. Chem. 1995, 60, 6678; (b) Marco, J. L.
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To a solution of b-ketosulfone (10 mmol) in acetic acid
(10 mL) was added iodine monochloride (11 mmol) and
the mixture stirred at room temperature for the appro-
priate time (Table 1). After completion of the reaction,
as monitored by TLC, the acetic acid was removed
under reduced pressure, water was added and product
extracted into ethyl acetate (3 · 10 mL). The combined
organic extracts were dried over anhydrous sodium sul-
fate and evaporated under reduced pressure to give the
crude product which was purified by silica column chro-
matography, eluting with 2:9 ethyl acetate and hexane.
Table 1, entry 2. White solid, mp = 149–150 ꢁC; 1H
NMR (300 MHz, CDCl3) d 2.50 (3H, s), 6.45 (1H, s),
7.40 (2H, d, J = 8.45 Hz), 7.45 (2H, d, J = 8.49 Hz)
7.49 (1H, t, J = 2.45 Hz), 7.75 (2H, d, J = 8.49 Hz)
7.85 (2H, d, J = 8.45 Hz); EIMS. m/z, M+ = 400.
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2.2. Synthesis of a-iodo methylsulfones
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To a solution of 10% aqueous NaOH (5 mL) was
added the a-iodo b-ketosulfone (5 mmol) at room tem-
perature and the mixture stirred for 30 min. After com-
pletion of the reaction as monitored by TLC, the
reaction was extracted into diethyl ether, the extract
dried over anhydrous sodium sulfate and evaporated
to give the corresponding crude a-iodo methylsulfone,
which was purified by column chromatography, eluting
with 1:9 ethyl acetate and hexane. Table 2, entry 2.
White solid, mp = 119–120 ꢁC; 1H NMR (300 MHz,
CDCl3) d 2.50 (3H, s), 4.41 (2H, s), 7.40 (2H, d,
J = 8.45 Hz), 7.85 (2H, d, J = 8.45 Hz); EIMS m/z
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Acknowledgements
The authors (V.S. and M.L.) are thankful to CSIR, New
Delhi for financial assistance and to Dr. J. S. Yadav,
Director IICT for his constant encouragement.
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