92248-06-1

10365-98-7

536-90-3

92248-06-1

General procedure for the synthesis of bis(3-methoxyphenyl)amines from 3-methoxyphenylboronic acid and m-aminoanisole: 1. copper acetate (2.1 mmol) and pyridine (0.25 mL) were added to a vigorously stirred solution of anhydrous dichloromethane (3.5 mL) of 3-methoxyaniline (1 mmol) and 3-methoxyphenylboronic acid (2 mmol) under nitrogen protection. 2. The reaction mixture was stirred at room temperature for 72 hours, during which time the progress of the reaction was monitored by thin layer chromatography (TLC). 3. Upon completion of the reaction, the crude reaction mixture was pre-adsorbed onto silica gel and the target product, bis(3-methoxyphenyl)amine (3c), was subsequently isolated by fast column chromatography. 4. Product yield: 25%; EI-MS m/z: 229 (M+) [Ref: Urgaonkar, S.; Verkade, J.G. J. Org. Chem. 2004, 69, 9135-9142].