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Synthesis 2003(6): 0841-0844
DOI: 10.1055/s-2003-38683
DOI: 10.1055/s-2003-38683
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Sodium Dithionite-Initiated Coupling of 1-Bromo-1-chloro-2,2,2-trifluoroethane with Pyrroles: A New, Convenient and Economical Synthesis of 5-(Trifluoromethyl)dipyrromethanes
Further Information
Received
31 January 2003
Publication Date:
16 April 2003 (online)
Publication History
Publication Date:
16 April 2003 (online)
Abstract
Sodium dithionite-initiated reactions of pyrrole and 1-methylpyrrole with 1-bromo-1-chloro-2,2,2-ethane in an acetonitrile-water mixture provide the respective 5-(trifluoromethyl)dipyrromethanes 1 and 3 as main products in 40-58% isolated yields and of high purity. Small amounts of tripyrranes 2 and 4 are also formed and could be isolated from the reaction mixtures.
Key words
5-(trifluoromethyl)dipyrromethanes - pyrroles - 1-bromo-1-chloro-2,2,2-trifluoroethane - sodium dithionite
- 1
Wijesekera TP. Can. J. Chem. 1996, 74: 1868 - 2
Nishino N.Wagner RW.Lindsey JS. J. Org. Chem. 1996, 61: 7534 - 3
Huang WY. J. Fluorine Chem. 1992, 58: 1 - 4
Huang WY.Wu FH. Israel J. Chem. 1999, 39: 167 - 5
Huang WY.Ma WP. Chin. J. Chem. 1992, 10: 180 ; Chem. Abstr. 1992, 117, 251010 - 6
Huang BN.Liu JT. J. Fluorine Chem. 1993, 64: 37 - 7
Plenkiewicz H.Dmowski W.LipiŇski M. J. Fluorine Chem. 2001, 111: 227 -
9a
Silverstein RM.Ryskiewicz EE.Willard C. Org. Synth., Coll.Vol IV Wiley; New York: 1963. p.821 -
9b
Kleinspehn GG.Briod AE. J. Org. Chem. 1961, 26: 1652 - 10
Sheldrick GM. Program for Crystal Structure Solution University of Göttingen; Göttingen: 1997. - 11
Sheldrick GM. Program for Refinement of Crystal Structures University of Göttingen; Göttingen: 1997. - 12
Farrugia LJ. J. Appl. Cryst. 2002, 32: 837
References
Dmowski, W.; Ignatowska, J. J. Fluorine Chem., in press.