Ethyl Acetate → 4-[4-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

Beteiligte Stoffe

Reaktionsschritte

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.42 g, 1.19 mmol), 4-bromo-2-fluorophenol (0.27 g, 1.43 mmol), cesium carbonate (0.78 g, 2.38 mmol), copper(II) trifluoromethanesulfonate (0.02 g, 0.06 mmol) and ethyl acetate (0.004 g, 0.06 mmol) in dry toluene (10 ml) are heated to reflux for 21 hours. The mixture is cooled to room temperature and N,N-dimethylformamide (2 ml) is added. The mixture is partitioned between 2M aqueous hydrochloric acid (10 ml) and ethyl acetate (3×10 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 4-[4-(4-bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

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