P-Anisidine → 2-Methoxy-N-(4-methoxyphenyl)aniline

Participants

Reaction Conditions

Reaction Steps

Anisidine (2.00 g, 16.2 mmol), 4-bromoaniline (3.34 g, 17.9 mmol), sodium tert-butoxide (2.34 g, 24.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.149 g, 0.162 mmol), and tri-tertbutylphosphine (0.053 g, 0.26 mmol) were put into a 100 mL 2-neck flask under nitrogen atmosphere, and 23 mL of anhydrous toluene was added thereto and stirred at 110° C. for 12 hours. When a reaction was completed, a reaction mixture was extracted with ethyl acetate, washed with salt water, and dried over MgSO4 to remove a solvent, followed by separation and purification using column chromatography (ethyl acetate/hexane=1/10), thereby obtaining the title compound (54%, 2.01 g) as a sticky solid.

Provenance & Evidence