Preparation of fluorohalophenols and N-acylfluorohaloanilines

Details Preparation of fluorohalophenols and N-acylfluorohaloanilines Preparation of fluorohalophenols and N-acylfluorohaloanilines

1991-11-08

1992-11-17

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 2, 546 3, 546 8, 546 9, 546 22, 558411, 564161, 564162, 568774, 568775, C07F 502

Patent

active

051645025

ABSTRACT:
Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.

REFERENCES:
Umemoto.sup.2 et al.sup.2, J. Org. Chemistry, 54, 1726-1731 (1989).
Haszeldine et al. Fluorine and its Compounds, Mathuen & Co. Ltd., pp. 116-123, 1951.
Halogen Compounds-Fluorine and Chlorine, vol. 5, Part 3, Houben-Weyl's Method of Chemistry, pp. 403-408, 1962.
March, Advanced Org. Chem., John Wiley & Sons, 3rd Edition, pp. 327, 510-511 1985.
T. Umemoto et al., Tetrahedron Letters, 27, 3271-3274 4465-4468 (1986).
T. Umemoto et al., Bull. Chem. Soc. Japan, 59, 3625-3629 (1986).

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