1,2-Dibromoethane → HCID 117966431, compound

Participants

Reaction Steps

To sodium hydride (2.29 g, 57 mmol, 60% dispersion in mineral oil) was added petroleum ether (40 mL). The suspension was stirred for 10 min and the supernatant was removed. Petroleum ether (40 mL) was added again and the suspension was stirred for another 10 min. The supernatant was removed again after the suspension settled in order to remove the mineral oil. Dimethylsulfoxide (25 mL) was slowly added at 20° C. under nitrogen. A solution of 2-(4-(methylthio)-1H-pyrazol-1-yl)acetonitrile (1.46 g, 9.53 mmol) and 1,2-dibromoethane (2.46 mL, 28.5 mmol) in dimethylsulfoxide (23 mL) was added dropwise over a period of 15 minutes. Additional 1,2-dibromoethane (0.5 mL) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into a cold saturated aqueous solution of ammonium chloride (150 mL). The mixture was stirred for 10 min and then it was extracted with diethyl ether (100 mL×3). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (95:5 to 60:40 heptane:ethyl acetate) to afford 1-(4-(methylthio)-1H-pyrazol-1-yl)cyclopropanecarbonitrile (390 mg, 22.8%). 1H NMR (500 MHz, CDCl3) δ 1.79-1.83 (m, 4H), 2.36 (s, 3H), 7.52 (s, 1H), 7.58-7.60 (m, 1H).

Provenance & Evidence