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Synthesis 2004(16): 2611-2613
DOI: 10.1055/s-2004-831230
DOI: 10.1055/s-2004-831230
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Improved Synthesis of 2,3-Dibromo-1-(phenylsulfonyl)-1-propene (DBP)
Further Information
Received
6 May 2004
Publication Date:
22 September 2004 (online)
Publication History
Publication Date:
22 September 2004 (online)
Abstract
A convenient preparation of 2,3-dibromo-1-(phenylsulfonyl)-1-propene (DBP, 1) is available through the one-pot propargylation and oxidation of thiophenol to give the propargyl sulfone 11, which is isomerized and brominated in another one-pot reaction. The new preparation is significantly more scalable, as well as more convenient and robust than the prior art.
Key words
sulfones - halogenation - alkynes - allenes - thiols
-
1a
Watterson SH.Ni Z.Murphree SS.Padwa A. Org. Synth. 1997, 74: 115 -
1b ‘2,3-Dibromo-1-(phenylsulfonyl)-propene’:
Reagents for Organic Synthesis
Vol. 16:
Fieser M. John Wiley & Sons; New York: 1992. p.107 - 2
Padwa A.Ishida M.Muller CL.Murphree SS. J. Org. Chem. 1992, 57: 1170 -
3a
Padwa A.Murphree SS.Yeske PE. J. Org. Chem. 1990, 55: 4241 -
3b
Padwa A.Austin DJ.Ishida M.Muller CM.Murphree SS.Yeske PE. J. Org. Chem. 1992, 57: 1161 -
4a
Padwa A.Muller CL.Rodriguez A.Watterson SH. Tetrahedron 1998, 54: 9651 -
4b
Murphree SS.Muller CL.Padwa A. Tetrahedron Lett. 1990, 31: 6145 -
5a
Guildford AJ.Turner RW. J. Chem. Soc., Chem. Commun. 1983, 466 -
5b
Denmark SE.Harmata MA.White KS. J. Org. Chem. 1987, 52: 4031 -
5c
Saito S.Hirayama K.Kabuto C.Yamamoto Y. J. Am. Chem. Soc. 2000, 122: 10776 - 6
Gupta BD.Roy S. Tetrahedron Lett. 1986, 27: 4905 - 7
Russell GA.Herold LL. J. Org. Chem. 1985, 50: 1037 - 8
Horner L.Binder V. Liebigs Ann. Chem. 1972, 757: 33 -
9a
Stirling CJM. J. Chem. Soc. 1964, 5863 -
9b
Pourcelot G.Cadiot P. Bull. Soc. Chim. Fr. 1966, 9: 3024 - 10
Barrett AGM.Dhanak D.Graboski GG.Taylor S. J. Org. Synth., Coll. Vol. VIII 1993, 550 - 11
Wildeman J.Van Leusen AM. Synthesis 1979, 733 - 12
Watanabe Y.Numata T.Oae S. Synthesis 1981, 204 -
13a
Hollingworth GJ. In Comprehensive Organic Functional Group Transformations Vol. 2:Katritzky AR.Meth-Cohn O.Rees CW.Pattenden G. Elsevier; Oxford: 1995. 144-152. p.154-156 -
13b
The Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides
Patai S.Rappoport Z. Wiley; New York: 1994. -
14a
Sato K.Hyodo M.Aoki M.Zheng X.-Q.Noyori R. Tetrahedron 2001, 2469 -
14b
Alonso DA.Nájera C.Varea M. Tetrahedron Lett. 2002, 43: 3459