Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester 


Vol. 22,  No. 4, pp. 269-273, Dec.  2016
10.7464/ksct.2016.22.4.269


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  Abstract

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.

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  Cite this article

[IEEE Style]

L. S and R. CS, "Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester," Clean Technology, vol. 22, no. 4, pp. 269-273, 2016. DOI: 10.7464/ksct.2016.22.4.269.

[ACM Style]

Lee S and Ra CS. 2016. Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester. Clean Technology, 22, 4, (2016), 269-273. DOI: 10.7464/ksct.2016.22.4.269.

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pISSN : 1598 - 9712
eISSN : 2288 - 0690

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