A new practical one-pot conversion of phenols to anilines.
A novel one-pot synthesis of anilines from phenols was developed. Using this methodology, anilines are produced in good yield (86%) by a reaction of phenols with 2-bromo-2-methylpropionamide and NaOH in DMA via Smiles rearrangement. Phenols, which are substituted electron-withdrawing groups, are more reactive for Smiles rearrangement. Thiophenols are also converted to anilines. The process is a convenient, safe, and inexpensive method for large-scale preparation of anilines. [reaction: see text]
Mizuno
Masahiro
M
Chemical Development Laboratories, Pharmaceutical Production Division, Takeda Pharmaceutical Company Limited, 17-85, Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan. Mizuno_Masahiro@takeda.co.jp
Yamano
Mitsuhisa
M