Sulfuric Acid → HCID 86720840, compound

Participants

Reaction Steps

Anthracene-9,10-diboronic acid (15.0 g, 56.4 mmol), palladium acetate (633 mg, 2.82 mmol), tri(t-butyl)phosphine (1.71 g, 8.46 mmol), methyl-1-bromonaphthalene-2-carboxylate (31.4 g, 118 mmol) and cesium carbonate (73.5 g, 226 mmol) were dissolved in 200 mL of xylene and the solution was reacted under reflux at the boiling point for 5 hours in a nitrogen atmosphere to obtain dimethyl-1,1′-(anthracene-9,10-diyl)bis(2-naphthoate) at a yield of 78%. Concentrated sulfuric acid (400 mL) was added to the dimethyl-1,1′-(anthracene-9,10-diyl)bis(2-naphthoate) (24.0 g, 44.0 mmol) to react at 180° C. for 4 hours. Thereafter, chloroform and water were added to the reaction mixture to separate the organic phase. The organic phase was washed with water and a saturated sodium chloride solution, and concentrated under reduced pressure. The resulting reaction mixture was purified by silica gel column chromatography (chloroform) to obtain dinaphtho[1,2-a:1′,2′-j]perylene-10,20-dione (yield: 28%) and dibenzo[a,o]naphtho[1,2,3,4-rst]pentaphene-7,10-dione (22%).

Provenance & Evidence