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NN-dimethyl-2-fluoro-2-phenylethylamine: preparation and solvolysis in aqueous acetone

1967; Royal Society of Chemistry; Linguagem: Inglês

10.1039/j39670000528

2050-5604

N. B. Chapman, R. M. Scrowston, Robert Westwood,

Chemical Reactions and Isotopes

Anhydrous potassium fluoride and ethyl α-bromophenylacetate in NN-dimethylformamide at 145–150° gave the corresponding α-fluoro-ester (53%), which was converted by alkaline hydrolysis and acidification, followed by reaction with thionyl chloride, into α-fluorophenylacetyl chloride (not isolated) and thence into the corresponding amide or NN-dimethylamide by conventional reactions. Diborane reduced the NN-dimethylamide to NN-dimethyl-2-fluoro-2-phenylethylamine (53%), also obtained by the action of dimethylamine on 1-bromo-2-fluoro-2-phenylethane. Reduction of the NN-dimethylamide with lithium aluminium hydride in ether gave a mixture of products.