Sodium Iodide → HCID 68992466, compound

Participants

Reaction Steps

To a suspension of 4′-fluoro-2′-hydroxyacetophenone (3.08 g), cesium carbonate (13.0 g) and sodium iodide (0.6 g) in N,N-dimethylformamide (20 mL) was added bromoethane (2.24 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To a solution of the residue and 4,4′-thiobis(6-tert-butyl -o-cresol) (39 mg) in methylene chloride (57.6 mL) was added 3-chloroperbenzoic acid (4.97 g) under ice-cooling, and the mixture was heated for reflux overnight. The reaction mixture was cooled in ice. To the mixture was added 10% aqueous sodium sulfite solution, and the resulting mixture was stirred for 20 minutes. The organic layer was separated and washed with water three times, a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (10 mL) -tetrahydrofuran (20 mL). To the solution was added sodium methoxide (28% methanol solution, 5 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 2-ethoxy-4-fluorophenol (3.0 g). The title compound was obtained in a similar manner to that described in Reference Example 142 using this material instead of 4-fluoro-2-methoxyphenol.

Provenance & Evidence