A novel synthetic method for preparation of bis(4-bromo-2,5-dialkoxyphenyl)methane and bis(4-nitro-2,5-dimethoxyphenyl)methane was reported. 1,4-Bis(ethoxymethyl)-2,5-dialkoxybenzene (1) was treated in boiling dichloromethane with catalytic amounts of p-toluenesulfonic acid gave pillar[5]arenes 2. 2 reacted with N-bromosuccinimide (NBS) in acetone under refluxing gave bis(4-bromo-2,5-dimethoxy- phenyl)methane (3). Nitration of 2 with nitric acid gave bis(4-nitro-2,5-dimethoxyphenyl)methane (4). This synthetic method has some advantages, such as mild reaction conditions, simple operation, high selectivity and good yield. The structures of 3 and 4 were confirmed by ¹H NMR, ¹³C NMR and MS techniques.

Key words: pillararene, N-bromosuccinimide, bromination, diphenylmethane