Title: Synthesis of 3,5-Dimethyl-4-bromoiodobenzene and 2,6Dimethyl-4-bromoiodobenzene
Abstract: Dimethyl-4-bromoiodobenzenes are aromatic organic intermediates used in many fields.In the presence of sodium percarbonate,4-iodo-2,6-dimethylaniline was obtained in 42.5% yield by reaction of 2,6-dimethylaniline with iodine in ethyl acetate at 45~50 ℃ for 1 h.Then,from 4-iodo-2,6-dimethylaniline,via diazotization at-5~0 ℃ and Sandmeyer reaction,3,5-dimethyl-4-bromoiodobenzene was obtained in 31.5% yield.4-Bromo-2,6-dimethyl aniline was obtained from the same starting material 2,6-dimethylaniline by reacting with hexamethylene tetramine-bromine complex for 0.5 h at room temperature,and the yield was 62.0%.Then 2,6-dimethyl-4-bromoiodobenzene was obtained in 33.1% yield from 4-bromo-2,6-dimethylaniline via diazotization at-5~0 ℃ and iodonation with KI.Structures of the intermediates and the final products were characterized by melting point,IR and 1HNMR.
Publication Year: 2008
Publication Date: 2008-01-01
Language: en
Type: article
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