Benzene, 1-bromo-3-(trifluoromethyl)- → [3-(Trifluoromethyl)phenyl](3-methoxyphenyl)amine

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PdOAc2 (8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (40 mg, 0.07 mmol) were added to a dried vial. The vial was caped with a septa-cap and inerted with nitrogen. Degassed anisole (2 mL)was added and the catalyst mixture was heated to 50ºC for 30 minutes, then cooled down to rt. A dry 2ml microwave vial was charged with sodium 2-methylpropan-2-olate (52 mg, 0.54 mmol). It was caped and inerted with nitrogen. A degassed mixture of 1-bromo-3-(trifluoromethyl)benzene (50 µL, 0.36 mmol) and 3-methoxyaniline (50 µL, 0.45 mmol) in anisole (2 mL) wad added at rt. The catalyst solution was added to the reaction mixture. The nitrogen inlet was removed and the vial was inserted into an alumina block at 100°C. The reaction was stirred over night. After 19h, the reaction was cooled down and filtered through celite. The filtrate was concentrated. Large amounts of anisole was present. No product was detected by LCMS. The sample was descarded.

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