1,2,4-Trimethylbenzene → Anthracene

Participants

Reaction Steps

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, o-biphenylboronic acid (0.9 g), Pd(OAc)2 (0.03 g), SPhos (manufactured by Aldrich Company) (0.12 g), potassium phosphate (1.7 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (14 ml) (pseudo cumene/t-butyl alcohol/water=10/3/1 (volume ratio)) were added to a flask and refluxed for 8 hours. Once the heating is completed, the reaction solution was cooled to room temperature. The reaction was terminated by adding water. The target compound was extracted with toluene. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel column chromatography (solvent: toluene) and further by active carbon column chromatography (solvent: toluene) to give 9-([1,1′-biphenyl]-2-yl)-10-([2,2′-binaphthalen]-7-yl)]anthracene (0.5 g) as the target compound represented by Formula (1-117). The scheme is shown in the following “Reaction 19”.

Provenance & Evidence