Dibenzofuran → HCID 21709773, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL three-neck flask was put 6.0 g (35 mmol) of dibenzofuran, and the air in the flask was replaced with nitrogen. To this flask was added 100 mL of tetrahydrofuran (abbreviation: THF), and this solution was cooled down to −80° C. Then, 22 mL (35 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dripped into this solution with a syringe. After that, this mixture solution was stirred for 2 hours while its temperature was increased to room temperature. After the stirring, the solution was cooled down to −80° C., 4.8 g (36 mmol) of copper(II) chloride was added thereto, and the mixture was stirred for 15 hours while its temperature was returned to room temperature. After the stirring, approximately 500 mL of water was added to this solution, followed by stirring for 1 hour to precipitate a solid. The precipitated solid was collected by suction filtration. The collected solid was dissolved in approximately 200 mL of hot toluene, this mixture was stirred and suction-filtered through Celite (Catalog No. 531-16855, produced by Wako Pure Chemical Industries, Ltd.), alumina, and Florisil (Catalog No. 540-00135, produced by Wako Pure Chemical Industries, Ltd.). The obtained filtrate was recrystallized from toluene/hexane to give 3.5 g of white powder, which was an objective substance, in 60% yield. Synthesis Scheme (c-1) of Step 1 is shown below.

Provenance & Evidence