Thionyl Chloride → HCID 21195971, compound

Participants

Reaction Steps

A solution of N-(2-hydroxyethyl)-5-bromo-2-fluorobenzamide (956 mg, 3.65 mmol) in methylene chloride was treated with thionyl chloride (0.35 ml, 4.75 mmol). The resulting mixture was stirred at ambient temperature as the progress of the reaction was monitored by thin layer chromatography. After one hour of stirring, no starting material was visible. The reaction mixture was diluted with methylene chloride, and the reaction was quenched by the addition of water and 1 N sodium hydroxide. The organic fraction was dried over sodium sulfate, and concentrated to a white solid. The solid was dissolved in 80% aqueous acetonitrile (25 ml) and an excess of potassium carbonate was added. The resulting mixture was stirred for about 72 hours at ambient temperature, heated to reflux for thirty hours, and worked up as before. The desired title product was then further purified by liquid chromatography, yielding 260 mg as a yellow oil.

Provenance & Evidence