Chloromethyl Methyl Ether → HCID 58047211, compound

Participants

Reaction Steps

To a solution of methyl 2-hydroxy-4-iodobenzoate (1.00 g, 3.60 mmol) and 1-ethoxy-4-ethynylbenzene (789 mg, 5.40 mmol) and copper(I) iodide (68.6 mg, 0.360 mmol) in triethylamine (9 mL) was added bis(triphenylphosphine)palladium(II) chloride (253 mg, 0.360 mmol), and the mixture was stirred under an argon stream at room temperature for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in DMF (10 mL). Potassium carbonate (2.59 g, 18.8 mmol) and chloromethyl methyl ether (1.07 mL, 14.0 mmol) were added thereto, and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to give the title compound (623 mg, yield 51%) as a yellow solid.

Provenance & Evidence