Bis(2-chloroethyl) ether → 4-(3-Chloro-4-fluorophenyl)-tetrahydro-pyran-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

NaH (60% in mineral oil, 14.3 g, 357 mmol) was suspended in NMP (143 mL) and cooled to 0° C. A solution of 1-chloro-2-(2-chloroethoxy)ethane (20.4 g, 143 mmol) and 3-chloro-4-fluorophenylacetonitrile (24.23 g, 143 mmol) in ether was then added dropwise via addition funnel. The resulting reaction mixture was stirred at 0° C. for 3 hours and then quenched with water, acidified with 5N HCl, diluted with 400 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed 3 times with 100 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title (16.99 g) after flash chromatography. MS m/e=240 (M+H)+.

Provenance & Evidence