Sodium Carbonate → 2-Bromoanthracene-9,10-dicarbaldehyde

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Reaction Steps

Diol intermediate 12a (1.58 g, 5.0 mmol, 1 equiv.) was dissolved in anhydrous acetonitrile (100 mL) and heated to reflux with stirring and formed a transparent, light-tan solution. Lead tetraacetate (4.42 g, 10.0 mmol, 2 equiv.) was added portion-wise to the solution over a period of 5 minutes, quickly turning the solution opaque and brown in color. The solution was then stirred at reflux for 4 hours, resulting in the formation of a dark-orange precipitate within the brown solution. The consumption of the diol intermediates were monitored through thin-layer chromatography (80% CH2Cl2/ethyl acetate, Rf=0.50 & Rf=0.33). After the reaction was complete, the reaction mixture was concentrated via rotary evaporation and gave a burgundy residue. 10% aqueous sodium carbonate (300 mL) was added to the residue, allowing the residue to be suspended in the aqueous solution. The organic contents were extracted from the aqueous layer using dichloromethane. The opaque, yellow organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow-orange solid residue. The residue was purified by column chromatography (20% ethyl acetate/hexane, Rf=0.29), providing 2-bromo-9,10-anthracenedialdehyde 13 as an orange solid (1.23 g, 80%). 1H NMR (CDCl3): δ 11.43 (s, 1H), 11.42 (s, 1H), 9.03 (s, 1H), 8.72 (m, 2H), 8.66 (d, 1H), 7.75 (m, 3H).

Provenance & Evidence