Bis(2-bromoethyl) ether → 4-(3,4-Dichlorophenyl)tetrahydro-2H-pyran-4-carbonitrile

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3,4-Dichlorophenylacetonitrile (10.00 g, 53.8 mmol) and bis(2-bromoethyl)ether (12.5 g, 53.8 mmol) were dissolved in ether and added dropwise via addition funnel to a suspension of NaH (60% dispersion in mineral oil; 6.45 g, 161 mmol) in 1-methylpyrrolidone (108 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and was then allowed to warm to ambient temperature. The reaction was then quenched with water. 5N HCl was added, and the reaction mixture was diluted with 200 mL of diethyl ether, added to a separatory funnel, washed 2 times with 100 mL of ether, separated, dried over Na2SO4, and concentrated in vacuo to give the purified title compound (7.97 g) after flash chromatography.

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