Thionyl Chloride → HCID 19835003, compound

Participants

Reaction Steps

A mixture of 7 g of 3-fluoro-2-[(3-fluorophenyloxy)methyl]benzoic acid and 50 g of thionyl chloride is refluxed with heating for 1 hour. After cooling to room temperature, dry toluene is added and the solvent is distilled off under reduced pressure. The residue is added with dichloromethane and the mixture is cooled to 0° C. Thereto 6 g of powdery anhydrous aluminum chloride is added and the mixture is stirred for 15 minutes and then added with ice-water, followed by extraction with toluene. After drying the extract over magnesium sulfate, the solvent is distilled off under reduced pressure. The residue is subjected to silica-gel chromatography and eluted with toluene to give 4.0 g of 3,7-difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 246(M+).

Provenance & Evidence