Isopropanol → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

Participants

Reaction Steps

A solution of 3.37 g (22.2 mmol) of 4-Chlorobenzyl cyanide and 4.93 g (24.4 mmol) of 1,3-dibromopropane in 15 mL of ether was added dropwise into 1.17 g (48.8 mmol) of NaH in 60 mL of DMSO. The temperature was held between 25° and 35° by water bath cooling. The mixture was stirred at room temperature for 18 hours. The mixture was cooled in ice water and 3 mL of 2-propanol was added dropwise, followed by the addition of 50 mL of water. The mixture was extracted with hexane (3×100 mL), and the combined extracts were washed with water (3×75 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 2.9 g (70%) product as colorless oil. 1H NMR (CDCl3) δ 2.04–2.15 (m, 1H), 2.39–2.52 (m, 1H), 2.55–2.65 (m, 2H), 2.79–2.88 (m, 2H), 7.38 (s, 4H). 13C NMR (CDCl3) 17.3, 34.9, 40.0, 124.2, 127.3, 129.4, 134.1, 138.6.

Provenance & Evidence