Clean Technology, Vol.22, No.4, 269-273, December, 2016
Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester
The benzylic bromination of methoxyimino-o-tolyl-acetic acid methyl ester (1) into (2-bromomethyl-phenyl)-methoxyiminoacetic acid methyl ester (2) using N-bromosuccinimide in the presence of 2,2'-azobisisobutyronitrile in various reaction solvents were investigated. The efficiency of the reaction was found to be sensitive to the kind of reaction solvents. We found the benzylic bromination of 1 to 2 can be performed in 1,2-dichlorobenzene as reaction solvent superior to the classic Wohl-Ziegler procedure in both reaction time and isolated yield (8 h vs 12 h, 92 vs 79%). This system provides clean, rapid, and high-yielding reactions with replacement of conventional solvents, such as tetrachloromethane, by less-toxic 1,2-dichlorobenzene.
Keywords:Benzylic radical bromination;Wohl-Ziegler procedure;1,2-dichlorobenzene;(2-bromomethyl-phenyl)-methoxyiminoacetic acid methyl ester
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