Sodium hydride → HCID 15860308, compound

Participants

Reaction Steps

(trans)-2-(2-Fluoro-5-methoxyphenyl)cyclopropane carbonitrile: To a suspension of NaH (1.73 g, 72 mmol) in DMSO (40 mL) was added solid trimethylsulfoxonium iodide (15.9 g, 72 mmol) in small portions. After the foaming had subsided (40 min), a solution of (trans)-3-(2-fluoro-5-methoxyphenyl)-2-propenenitrile (4.26 g, 24 mmol) in DMSO (10 mL) was added dropwise, maintaining the temperature between 35°-40° C. Stirring was continued for 18 h at room temperature, followed by the dropwise addition of saturated NH4Cl (100 mL) and extraction with ethyl acetate. The organics were combined, washed with brine, dried (K2CO3), and concentrated to give a red oil which was then purified by silica gel chromatography (CH2 Cl2 /hexane, 60:40) to afford the title compound as a clear oil (46% yield): 1H NMR (300 MHz, CDCl3) δ0.82-0.88 (m, 2H), 1.65-1.75 (m, 1H), 2.55-2.62 (m, 1H), 3.75 (s, 3H), 6.50-6.55 (m, 1H), 6.60-6.70 (m, 1H), 6.92 (t, J=6.5 Hz, 1H).

Provenance & Evidence