Synthesis of Rubicene via Scholl Reaction Using DDQ and TfOH
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This TCI Practical Example describes the synthesis of rubicene through the Scholl reaction, using 9,10-diphenylanthracene [D1689] as the starting material together with DDQ [D1070] and trifluoromethanesulfonic acid (TfOH) [T0751]. In the procedure carried out in dichloromethane at 0 °C for 1 hour, 9,10-diphenylanthracene (200 mg, 0.61 mmol) was treated with DDQ (3.0 eq.) and TfOH, then quenched with saturated aqueous NaHCO3, filtered through celite, and purified by silica gel column chromatography. Rubicene was obtained as a red solid in 67% yield (131 mg). The reaction mixture changed from yellow to blue after adding TfOH, and to red after quenching with saturated aqueous NaHCO3. The reaction was monitored by TLC (hexane:dichloromethane = 3:2, Rf = 0.37), and rubicene was characterized by ¹H NMR (270 MHz, CDCl3).
Related products
- TCI D1070 84-58-2 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- TCI T0751 1493-13-6 Trifluoromethanesulfonic Acid
- TCI D1689 1499-10-1 9,10-Diphenylanthracene
Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20250310
- TCI product page D1070: tcichemicals.com/ID/en/p/D1070
For research and laboratory use only, not for human consumption.
