Continuous flow reaction system for the synthesis of 2,2,2-trichloroacetophenone derivatives and its application

Byeng Ha Ko; Subeen Yu; Kwang Ho Song; Sunwoo Lee

doi:10.1016/j.tetlet.2018.01.067

Continuous flow reaction system for the synthesis of 2,2,2-trichloroacetophenone derivatives and its application

Byeng Ha Ko, Subeen Yu, Kwang Ho Song, Sunwoo Lee

Department of Chemical and Biological Engineering

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

A continuous flow reaction system was developed for the synthesis of 2,2,2-trichloroacetophenone derivatives. When aryl propiolic acids and water were mixed with trichloroisocyanuric acid in DMF at 5 °C, the 2,2,2-trichloroacetophenone derivatives were formed within 5 min with good yields. In addition, the resulting mixture was flowed to react with amines to give the corresponding benzamide. This flow reaction system provided higher yields within shorter times than the batch reaction system.

Original language	English
Pages (from-to)	991-994
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2018.01.067
Publication status	Published - 2018 Mar 14

Keywords

Decarboxylative chlorination
Flow chemistry
Propiolic acid
Trichloroacetophenone
Trichloroisocyanuric acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.01.067

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title = "Continuous flow reaction system for the synthesis of 2,2,2-trichloroacetophenone derivatives and its application",

abstract = "A continuous flow reaction system was developed for the synthesis of 2,2,2-trichloroacetophenone derivatives. When aryl propiolic acids and water were mixed with trichloroisocyanuric acid in DMF at 5 °C, the 2,2,2-trichloroacetophenone derivatives were formed within 5 min with good yields. In addition, the resulting mixture was flowed to react with amines to give the corresponding benzamide. This flow reaction system provided higher yields within shorter times than the batch reaction system.",

keywords = "Decarboxylative chlorination, Flow chemistry, Propiolic acid, Trichloroacetophenone, Trichloroisocyanuric acid",

author = "Ko, {Byeng Ha} and Subeen Yu and Song, {Kwang Ho} and Sunwoo Lee",

note = "Funding Information: This research was supported by Korea University and a National Research Foundation of Korea (NRF) grant provided by the Korean government ( MSIP ) (NRF-2015R1A4A1041036). Spectral data were obtained from the Korea Basic Science Institute, Gwangju branch. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2018.01.067",

language = "English",

volume = "59",

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journal = "Tetrahedron Letters",

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AU - Yu, Subeen

AU - Song, Kwang Ho

AU - Lee, Sunwoo

N1 - Funding Information: This research was supported by Korea University and a National Research Foundation of Korea (NRF) grant provided by the Korean government ( MSIP ) (NRF-2015R1A4A1041036). Spectral data were obtained from the Korea Basic Science Institute, Gwangju branch. Publisher Copyright: © 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/3/14

Y1 - 2018/3/14

N2 - A continuous flow reaction system was developed for the synthesis of 2,2,2-trichloroacetophenone derivatives. When aryl propiolic acids and water were mixed with trichloroisocyanuric acid in DMF at 5 °C, the 2,2,2-trichloroacetophenone derivatives were formed within 5 min with good yields. In addition, the resulting mixture was flowed to react with amines to give the corresponding benzamide. This flow reaction system provided higher yields within shorter times than the batch reaction system.

AB - A continuous flow reaction system was developed for the synthesis of 2,2,2-trichloroacetophenone derivatives. When aryl propiolic acids and water were mixed with trichloroisocyanuric acid in DMF at 5 °C, the 2,2,2-trichloroacetophenone derivatives were formed within 5 min with good yields. In addition, the resulting mixture was flowed to react with amines to give the corresponding benzamide. This flow reaction system provided higher yields within shorter times than the batch reaction system.

KW - Decarboxylative chlorination

KW - Flow chemistry

KW - Propiolic acid

KW - Trichloroacetophenone

KW - Trichloroisocyanuric acid

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Continuous flow reaction system for the synthesis of 2,2,2-trichloroacetophenone derivatives and its application

Abstract

Keywords

ASJC Scopus subject areas

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