Phenol → 2-Phenoxy-6-(phenylamino)benzonitrile

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Sodium phenoxide was generated by dissolving phenol (0.36 g, 3.83 mmol) in dry tetrahydrofuran (5 mL), and adding sodium hydride (0.087 g, 3.6 mmol). After gas evolution ceased, the solvent was evaporated and 2-fluoro-6-(phenylamino)benzonitrile (0.6 g, 2.83 mmol) dissolved in dimethyl sulfoxide (10 mL) was added. The mixture was heated to 110° C. while stirring under argon for 4 hours. The solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water (5×), brine (1×) dried over anhydrous Na2SO4 filtered, and evaporated to give the crude product which was then chromatographed on silica gel eluted with 10–40% CH2Cl2 in hexane to give the title compound as a white amorphous solid. mp 146–147° C.

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