Phenol → HCID 22136223, compound

Participants

Reaction Conditions

Reaction Steps

Phenol (2.06 g, 22 mmol) was dissolved in dry dimethyl sulfoxide (25 mL), and sodium hydride (0.53 g, 22 mmol) was added in portions, and the mixture stirred for 1 hour under argon. 2-Amino-6-fluorobenzonitrile (2.72 g, 20 mmol) was added and the mixture heated to 110° C. overnight. 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 0–20% ethyl acetate in hexane to give the title compound as a white amorphous solid. Recrystallization from carbon tetrachloride, hexane gave a white crystalline solid. mp 66–67° C.

Provenance & Evidence