Trifluoromethyltoluene

Fluorotoluene can be deprotonated in the benzylic position by the superbases, but the halogen appears to offer little activation to the process. 2-Trifluoromethyltoluene is more readily deprotonated, but decomposes by elimination of fluoride even at — 100°C . 

Bromo-p-phenylenediamine hydrochloride (0.07 mol) and di-t-butyl-dicarbonate (0.15 mol) were dissolved in 250 ml apiece of 2 M NaOH and trifluoromethyltoluene, heated to 45 °C, and stirred 3 days. Thereafter, additional di-t-butyl dicarbonate (0.14 mol) was added, the layers separated, and the aqueous phase extracted with CH2CI2. The combined extracts were evaporated to dryness and the residue mixed with 200 ml hexane. The precipitate was filtered, washed, and the product isolated in 82% yield, mp = 130°C. 

Trifluoromethyl-substituted phenylacetic and mandelic acids undergo efficient photodecarboxylation in basic aqueous solution, to give the corresponding trifluoromethyltoluenes or trifluoromethylbenzyl alcohols. This is consistent with formation of benzylic carbanions that subsequently react with water. Quenching studies support a reaction mechanism involving the singlet excited state. 

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