Ethylmagnesium chloride 2- phenyl

A solution of 2-(pyrazol-l-yl)phenylmagnesium bromide in THF (350 ml) is prepared by metallation of 1-phenylpyrazole (86.5 g, 0.6 mol) by ethylmagnesium bromide [9] and stirred and maintained at 25-30° as a solution of benzonitrile (51.6 g, 0.5 mol) in THF (150 ml) is added rapidly. The mixture is heated under reflux for 6 h, cooled, and poured into a solution of ammonium chloride (120 g) in water (1 litre). The solution is extracted with ether, and the ether phase is extracted with 2 m hydrochloric acid (total 600 ml). (Evaporation of the ether phase then leaves 1-phenylpyrazole (40 g)). The acid extract is (without filtration from the crystals which precipitate) treated with 10 m sodium hydroxide (300 ml) and extracted with ether. Evaporation of the extract gives phenyl 2-(pyrazol-l-yl)phenyl ketimine (99 g, 80% based on benzonitrile), m.p. 106-107°. 

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