Pyridine → HCID 12182452, compound

Participants

Reaction Steps

To a suspension of the anhydrous sodium salt of 206 g of 2,4-difluorophenol in 400 ml of diethylene glycol dimethyl ether are added 5 g of copper powder, 5 g of copper(I) iodide, 8 ml of pyridine and 393 g of 4-bromoanisole. With stirring, the reaction mixture is heated, under nitrogen, for 17 hours to 150°-155° C. After cooling, the reaction mixture is filtered over Hyflo and the bulk of the solvent is removed by vacuum distillation. The residue is dissolved in ether and the ethereal solution is washed repeatedly with 10% aqueous sodium hydroxide and then with water. The ethereal solution is dried over sodium sulfate and the solvent is removed by distillation. The residue is purified by chromatography over silica gel (eluant: 8:1 mixture of petroleum ether/diethyl ether). The solvent is removed by evaporation, to give the title compound in the form of a residual oil; nD22 =1.5466.

Provenance & Evidence