Tetrahydrofuran → HCID 15915434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dimethylfuran (1.06 mL, 10 mmol) in anhydrous THF (10 mL) was added magnesium powder (0.292 g, 12 mmol). The reaction mixture was heated to reflux for 5 minutes. The reaction flask was placed in a room temperature oil bath and a solution of 1-bromo-2-fluorobenzene (1.08 mL, 10 mmol) in anhydrous THF (10 mL) was added. The reaction mixture was heated to 35° C. for 1 hour, heated to reflux over 1 hour, and stirred at reflux for 1 hour. The reaction mixture was cooled and poured into saturated ammonium chloride solution and diluted with water. The product was extracted with ethyl acetate (2×) and the combined organic layer dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give the desired product.

Provenance & Evidence