11α-Hydroxy-19-nor-steroids react with N-(2-chloro-1,1,2-trifluoroethyl)diethylamine to give the 11β-fluoro-derivatives or, in presence of lithium chloride or lithium bromide, the 11β-chloro- and 11β-bromo-derivatives, respectively.
E. J. Bailey, H. Fazakerley, M. E. Hill, C. E. Newall, G. H. Phillipps, L. Stephenson and A. Tulley, J. Chem. Soc. D, 1970, 106 DOI: 10.1039/C29700000106
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