Pyridine → 1-Nitrodibenzofuran

Participants

Reaction Steps

In a flame dried 3-neck flask, CuI (10.3 g, 54.3 mmol) and tBuOK (6.7 g, 60 mmol) were stirred in 120 mL dimethoxyethane for 1 h. To the stirred solution was added 280 mL pyridine and the solution turn purplish. In a separate flask 2-iodophenol (24.1 g, 109 mmol) and tBuOK (12.9 g, 115 mmol) were dissolved in 60 mL dimethoxyethane and transferred to the reaction flask. Solid 2,4-dinitrodibenzofuran (16 g, 95 mmol) was then immediately added to the reaction flask and stirred for 10 minutes. Reaction mixture was then refluxed for 2.5 h. After completion, reaction mixture was cooled and carefully quenched with 8M H2SO4. Dark color solution was filtered thru a Celite and the filtrate was partitioned between ethylacetate and water. Aqueous layer was extracted twice with ethylacetate. Combined organic layer was washed with sodium sulfite solution followed by Na2CO3 solution and dried over anhydrous Na2SO4. Organic solvent was removed under vacuum. Crude product was purified by flash chromatography over silica gel with 20% DCM/Hexanes. Target compound (13 g, 64% yield) was isolated as yellow solid upon evaporation of organic solvent under vacuum.

Provenance & Evidence