Potassium Carbonate → 1-Iodo-4-(2-methyl-3-butyn-2-yloxy)-2-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

3-Chloro-3-methyl-1-butyne (640 μL, 5.7 mmol, 3.0 equiv) was added to a stirred solution of 4-iodo-3-nitrophenol (500 mg, 1.89 mmol, 1 equiv), tetrabutylammonium iodide (2.10 g, 5.7 mmol, 3.0 equiv), and potassium carbonate (522 mg, 3.8 mmol, 2.0 equiv) in acetone (5.2 mL) at 23° C. The reaction mixture was warmed to 65° C. and was heated at this temperature for 18 h. The product solution was allowed to cool to 23° C., then was diluted with ethyl acetate (50 mL). The diluted product solution was washed with saturated aqueous sodium bicarbonate solution (5 mL) and saturated aqueous sodium chloride solution (5 mL). After washing, the organic layer was dried over sodium sulfate and the solids were filtered. The filtrate was concentrated. The residue obtained was dissolved in ethyl acetate (10 mL) and the resulting solution was filtered through a pad of Celite, eluting with ethyl acetate (50 mL). The eluent was concentrated and the residue obtained was purified by flash-column chromatography (4% acetone-hexanes) to furnish 1-iodo-4-(2-methyl-3-butyn-2-yloxy)-2-nitrobenzene as a pale yellow oil (569 mg, 91%).

Provenance & Evidence