Phenylmagnesium bromide, reaction with nitriles

The Bradsher reactionl49 jg a synthetic route that converts aryl ketones (234) to polycyclic hydrocarbons such as 235. This reaction can also be applied to heterocyclic derivatives of 234 (X = O, S, Se). A common route to ketones such as 234 is shown for the preparation of 240. Two of the aryl groups are incorporated by a Grignard reaction of aldehyde 236 with phenylmagnesium bromide, producing 237 in 81% yield. Subsequent treatment with cuprous cyanide (also see sec. 2.1 l.E) leads to nitrile 238, and reaction with ethylmagnesium bromide gives the ketone precursor (239). Subsequent reaction with HBr (reflux for four... 

Finally, the reaction of nitriles with Grignard reagent was also recommended, leading eventually to ketones which can be easily identified. The method is especially suitable for the identification of low-molecular nitriles phenylmagnesium bromide (61) is used for the Grignard reaction... 

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