US EPA

7701082 

Journal Article 

SYNTHESIS OF AROMATIC FLUORO COMPOUNDS BY NUCLEOPHILIC EXCHANGE OF NITRO-GROUPS BY FLUORIDE 

Effenberger, F; Streicher, W; , 

1991 

1 

Chemische Berichte
ISSN: 0009-2940 

VCH PUBLISHERS INC 

DEERFIELD BEACH 

124 

1 

157-162 

German 

10.1002/cber.19911240124 

WOS:A1991EW17700023 

The synthesis of aromatic fluoro compounds from the respective nitro compounds by nucleophilic substitution of nitrite by fluoride is described. Reasonable yields in case of nonactivated nitro compounds are only obtained if the nitrite formed in the reaction is eliminated by acylation. 1-Fluoro-3-nitrobenzene (2) was obtained from 1,3-dinitrobenzene (1), and 1-fluoro-3,5-dinitrobenzene (9) as well as 1,3-difluoro-5-nitrobenzene (10) from 1,3,5-trinitrobenzene (8) in yields up to 92% by reaction of nitro compounds with potassium fluoride in sulfolane at 180-200-degrees-C in the presence of phthaloyl dichloride (6); 1,2-difluoro-4-nitrobenzene (12) was formed in 58% yield from 2,4-dinitro-1-fluorobenzene (11) in the presence of pyromellitoyl tetrachloride (13). 

FLUORO COMPOUNDS, AROMATIC; NITRITE EXCHANGE BY FLUORIDE