Dimethyl Sulfoxide → 1-[4-(Trifluoromethoxy)phenyl]cyclobutanecarbonitrile

Participants

Reaction Steps

To sodium hydride (4.4 g, 110 mmol) was slowly added DMSO (100 mL) at 0° C. The mixture was warmed to room temperature and stirred for 10 minutes. A solution of 2-(4-(trifluoromethoxy)phenyl)acetonitrile (10.05 g, 50 mmol) and 1,3-dibromopropane (11.0 g, 55 mmol) in diethyl ether (50 ml) was added over 30 min at ≦30° C. Near the end of the addition, the mixture became very thick purple slurry that could not be stirred. An additional 50 mL of DMSO was added. After stirring for 75 min at room temperature, the reaction was complete according to LCMS. The reaction mixture was diluted with 25 mL of isopropanol and 15 mL of water, and extracted with ether. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated to give the title compound. (10.85 g yield 90%).

Provenance & Evidence