Ethanol → 1-Chloro-3-fluoro-5-(2-nitroethyl)benzene

Participants

Reaction Steps

Add sodium borohydride (0.75 g, 19.7 mmol) to a solution of 1,4-dioxane (10 mL) and absolute ethanol (2.5 mL) in a room temperature water bath. Next add 1-chloro-3-fluoro-5-((E)-2-nitrovinyl)-benzene (1.5 g, 8.98 mmol) in 1,4-dioxane (10 mL) dropwise and stir at room temperature for 1 hour (Bhattacharjya, Synthesis, 1985, 886-997). Add ice chips, glacial acetic acid (2 mL), water (2 mL), concentrate and dilute in dichloromethane/water. Wash the dichloromethane layer with water, saturated aqueous sodium chloride, dry (sodium sulfate), filter and purify (silica gel chromatography, eluting with 1:1 dichloromethane:hexanes) to give the desired compound as an oil (1.07 g 70%).

Provenance & Evidence