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Synthesis of 3-chloroindole and 3-bromoindole.

JJ Jehyun Jeon
JL Jaehee Lee
SJ Se-Min Jung
JS Jae Hong Shin
WS Woon Ju Song
MR Mina Rho
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To isolate large quantities of 2,3-dichloroindole and 2,3-dibromoindole for 1H and 13C NMR experiments, we synthesized 3-chloroindole or 3-bromoindole and used as the substrate for the reactions with Hal1. To a dried 50-ml round-bottom flask, 588 mg of indole (1 eq) and 377 μl of 1,4-dimethylpiperazine (0.558 eq) were dissolved into 5 ml DCM. The temperature was lowered by placing the flask in iced water. After 10 min, 800 mg of N-chlorosuccinimide or N-bromosuccinimide (0.9 eq) was added slowly and stirred for 15 min to yield 3-chloroindole or 3-bromoindole, respectively. After 15 min, the temperature was raised to room temperature, and the reaction mixture was stirred for 3 h. Volatile fractions were removed by rotary evaporation, and the product was isolated by silica chromatography (ethyl acetate-hexane, 5:95). The isolated yields of 3-chloroindole and 3-bromoindole were 55.5% and 57%, respectively.

Copyright and License information:  ©2021 Jeon et al.
This is an open-access article distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.This content is distributed under the terms of the Creative Commons Attribution 4.0 International license.

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