REACTION OF 3-INDOLYLPHENYLIODONIUM BETAINE WITH ELECTROPHILIC AGENTS

Article abstract of DOI:10.1007/BF00506459

3-Indolylphenyliodonium chloride and bromide, respectively, were obtained by the action of hydrochloric and hydrobromic acids on 3-indolylphenyliodonium betaine.Pyrolysis of the chloride leads to a mixture of 2- and 3-chloroindoles,while pyrolysis the bromine leads only to 3-bromoindole. 1-Benzyl-2-chloroindole is obtained in the reaction of the betaine with benzyl chloride.The betaine reacts with dimethylsulfate to give an iodonium salt, the reaction of wich with lithium chloride and ammonium chloride leads to 1-methyl-2-chloroindole.