2-bromo-1-(2-hydroxy-6-methylphenyl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium fluoride (0.85 g, 14.7 mmol) was added to a solution of 2-bromo-1-(2-hydroxy-6-methylphenyl)ethan-1-one (26b) (1.5 g, 6.5 mmol) in anhydrous dimethylformamide (25 mL). The reaction mixture was stirred at room temperature for 4 days. Ethyl acetate (75 mL) was added and the mixture was washed with brine (3×100 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20) to provide the desired benzofuran-3-one (26c) (450 mg, 3.04 mmol, 46%). the mixture was washed with brine (3×100 mL) The organic layer was dried over sodium sulfate evaporated to dryness The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium fluoride (0.85 g, 14.7 mmol) was added to a solution of 2-bromo-1-(2-hydroxy-6-methylphenyl)ethan-1-one (26b) (1.5 g, 6.5 mmol) in anhydrous dimethylformamide (25 mL). The reaction mixture was stirred at room temperature for 4 days. Ethyl acetate (75 mL) was added and the mixture was washed with brine (3×100 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20) to provide the desired benzofuran-3-one (26c) (450 mg, 3.04 mmol, 46%). the mixture was washed with brine (3×100 mL) The organic layer was dried over sodium sulfate evaporated to dryness The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20)