7135-31-1

Upstream product

• 67765-96-2 phenyl (β-indolyl)iodonium trifluoroacetate 

Downstream Products

• 1419612-82-0 1-(2-chloro-1H-indol-3-yl)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1419612-83-1 2-(4-bromophenyl)-1-(2-chloro-1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline 
• 1419612-84-2 1-(2-chloro-1H-indol-3-yl)-2-p-tolyl-1,2,3,4-tetrahydroisoquinoline 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 

Relevant academic research and scientific papers

PECULIARITIES OF NUCLEOPHILIC SUBSTITUTION IN INDOLYLIODONIUM SALTS

3-Indolylphenyliodoniun trifluoroacetate reacts with ammonium bromide and lithium chloride and bromide to give 3-haloindoles.The reaction with ammonium chloride and tetrabutylammonium chloride leads to a mixture of 2- and 3-chloroindoles.The same mixture of chloroindoles is also formed by the action of lithium chloride but in the presence of 15-crown-5 ether.The course of the reaction is explained by ambident reaction of the iodonium salt.

REACTION OF 3-INDOLYLPHENYLIODONIUM BETAINE WITH ELECTROPHILIC AGENTS

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.