CAS: 31558-41-5; 4-Bromo-2,5-Dimethoxybenzaldehyde

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2-(2',5'-Dimethoxyphenyl)-1,3-Dioxolane置于三甲基溴硅烷,碘苯二乙酸体系中,用38%的收率获得产物4-溴-2,5-二甲氧基苯甲醛
参考文献:Hypervalent Iodine Chemistry: Mechanistic Investigation Of The Novel Haloacetoxylation,Halogenation,And Acetoxylation Reactions Of 1,4-Dimethoxynaphthalenes
标题:Hypervalent Iodine Chemistry: Mechanistic Investigation Of The Novel Haloacetoxylation,Halogenation,And Acetoxylation Reactions Of 1,4-Dimethoxynaphthalenes
摘要:Treatment Of 1,4-Dimethoxynaphthalenes With Iodosobenzene Diacetate And Trimethylsilyl Chloride Or Bromide Furnished The Haloacetoxylated,Acetoxylated,And Halogenated 1,4-Dimethoxynaphthalenes In Excellent Yield. The Reaction Pathway For Each Transformation Was Shown To Be A Function Of Reagent Stoichiometry. A Mechanistic Hypothesis Is Presented That Rationalizes The Reaction Pathways And Explains The Subtle Differences In The Halogenation Reactions. The Acetoxylation,For Example,Is Thought To Involve The Formation Of An Iodonium Ion That Promotes The Nucleophilic Addition Of Acetate Ion And Subsequent 1,2-Acetyl Migration. Bromination occurs As A Direct Result Of The Oxidation Of Trimethylsilyl Bromide To Bromine,Followed By Electrophilic Aromatic Substitution. Chlorination Is Thought To Proceed Via A Radical Process And Not The Formation Of Molecular Chlorine From The Dissociation Of Iodosobenzene Dichloride. The Haloacetoxylation Reaction Also Appears To Be Fairly Specific For 1,4-Dimethoxynaphthalenes,Since The Analogous Reaction With A 1,4-Dimethoxybenzene Derivative Was Unsuccessful.
DOI:10.1021/jo970525I