1- nitro-4-trifluoromethyl benzene

Nitration of (trifluoromethyl)benzene on the other hand yields almost exclusively m nitro(trifluoromethyl)benzene (91%) The ortho and para substituted isomers are minor components of the reaction mixture... 

Nitro-2-(trifluoromethyl)benzene [o-Nitro(trifluoromethyl)benzene]... 

Trifluoromethyl)benzene o Nitro(tnfluoro rn Nitro(tnfluoro p Nitro(tnfluoro... 

FIGURE 12 11 Comparative energy diagrams for nitro mum ion attack on (a) ben zene and at the (b) ortho (c) meta and d) para posi tions of (trifluoromethyl) benzene fact (ortho) > fact (para) > fact (meta) >... 

Trifluoromethyl)benzene (benzotrifluoride, 15) was the first organic fluoride to incorporate a trifluoromethyl group. By a standard nitration process, it formed l-nitro-3-(trifluoromethyl)-benzene (16) which was reduced to the 1-amino derivative, 17. This we a-directive influence on electrophilic aromatic substitution contrasted with that for fluorobenzene, which gave 4-and 2-nitro products. 

Similarly, only by using phthaloyl chloride as the trapping agent for the eliminated nitrite ion, could 3,5-dinitro-l-(trifluoromethyl)benzene (13) be converted to 3-fluoro-5-nitro-l-(trif-luoromethyl)benzene (14) in good yield.141... 

Trifluoromethyl copper reacts with 4-chloro-3-nitrobenzotrifluoride in position 4. The carbanion of the organocopper compound, trifluoromethyl, attacks this position, because as a very strong nucleophile, it joins the carbon of the lowest electron density. The electron density of position 4 is decreased by the trifluoromethyl group in para position, and even more strongly by the nitro group in ortho position. The product is K, 3-nitro-1,4-bis-(trifluoromethyl)benzene [115]. 

Treatment of 2,2,2-trifluoro-] -phenylethanone (6) and (trifluoromethyl)benzene (8) with ozone or ozonized air in chlorinated hydrocarbons, and in the presence of excess nitrogen dioxide and a catalytic amount of an iron(Hl) salt at - 10 to O C, leads to the respective nitro compounds 7 and 9 in good to excellent yields. The reaction is clean and rapid, and little or no hydrolysis of the trifluoromethyl moiety is observed during the nitration. ... 

Kluoro-l-nitro-2-(trifluoromethyl)benzene (2) Typical Procedure 1... 

When the nitration of (trifluoromethyl)benzene was carried out with nitronium tetrafluoroborate at -80 °C, Olah was able to isolate the Wlieland intermediate 1 (Scheme 7.2). Subsequent warming resulted in the formation of l-nitro-3-(trifluoromethyl)benzene. 

C7H4CIFO 4-chloro-2-fluorobenzaldehyde 51072-56-f 25.00 1.3310 2 9800 C7H4F3N02 1-nitro-2- trifluoromethyl)benzene 384-22-5 25.00 1.3910 2... 

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