1,2-Dimethoxyethane → 3,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene

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Reaction Steps

Under a nitrogen stream, a 300-mL three-necked flask was charged with 8.15 g (18.7 mmol) of 2,7-dibromo-3,6-di-t-butyl-fluorene and 1.08 g (0.93 mmol) of Pd(PPh3), and further charged with 120 ml of 1,2-dimethoxyethane. The mixture was stirred at room temperature for 20 minutes. To this solution, 20 ml of an ethanol solution in which 5.01 g (41.1 mmol) of phenylboric acid was dissolved was added, and the mixture was stirred at room temperature for 20 minutes. Thereafter, 37.4 ml (74.8 mmol) of a 2.0 mol/L aqueous solution of sodium carbonate was added. Subsequently, the mixture was heated to reflux for 18 hours, left to be naturally cooled, and quenched with dilute hydrochloric acid in an ice bath. Thereafter, ether was added to extract the soluble fraction, and the organic layer was washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water, and two times with saturated brine, and then dried over magnesium sulfate. Then, magnesium sulfate was separated by filtration, and the filtrate distillation under reduced pressure using a rotary evaporator to remove the solvent. The resulting solids were purified by column chromatography to obtain a target product (yield 4.36 g (54%)). The target product was identified by 1H-NMR and FD-MS spectroscopy.

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