Preparation of fluorohalophenols and N-acyfluorohaloanilines

Details Preparation of fluorohalophenols and N-acyfluorohaloanilines Preparation of fluorohalophenols and N-acyfluorohaloanilines

1990-08-06

1992-05-26

Hollrah, Glennon H.

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

051169827

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:
T. Umemoto et al., Bull. Chem. Soc. Japan, 59, 3625-3629 (1986).
J. March, Advanced Organic Chemistry, 3rd Ed., 510-511, (1985).
T. Umemoto et al., Tetrahedron Letters, vol. 27, 3271-3274, 4465-4468 (1986).
T. Umemoto et al., J. Organic Chemistry, 54, 1726-1731 (1989).
Taub, Chemistry and Industry, 1962, pp. 558-559.

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