Thionyl Chloride → 3,9-Difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one

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Reaction Steps

To 10 g of 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoic acid is added 50 g of thionyl chloride and the mixture is refluxed with heating for 1 hour. After cooling the reaction mixture to room temperature, dry toluene is added and the solvent is distilled off under reduced pressure. The residue is added with dichloromethane and cooled to 0° C. Thereto 10 g of powdery anhydrous aluminum chloride is added and the mixture is stirred for 15 minutes. The reaction mixture is added with ice-water and extracted with toluene. After the extract is dried over magnesium fulfate, the solvent is distilled off under reduced pressure and the residue is subjected to silica-gel chromatography, followed by elution with toluene to give 4.3 g of 3,9-difluoro-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 246(M+).

Provenance & Evidence