Halides, acyl, base induced

As an example of their use in organic chemistry, the analgesic drug Pravadoline has been synthesized in two steps using 1-butyl-3-methylimidazolium hexafluorophosphate, abbreviated [bmimllPF J, as the solvent for both steps. The first step is a base-induced reaction of 2-methylindole with a primary alkyl halide, and the second is a F riedel-Crafts acylation. Both steps take place in 95% yield, and the ionic solvent is recovered simply by washing the reaction mixture, first with toluene and then wMth water. We ll be hearing a lot more about ionic solvents in coming years. 

Stirring these acyl compounds with a base such as sodium ethoxide in dry ethanol solution. The presence of an electron-withdrawing substituent appears to drastically decrease the rate a complex di-p-chloro-bis[MA -dimethyl-5-chlorobenzylamino-2C,Andipalladium(ll) is recovered unchanged after 3 days under reflux under the same reaction conditions. These reactions are presumed to proceed through a two-step process in which the first step is the insertion of acyl halides and the second is the potassium cyanide-induced dissociation of the presumed intermediates 7.37 [76,88]. 

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