Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane

Chang Hee Lee; Soo Min Lee; Byul Hana Min; Dong Su Kim; Chul Ho Jun

doi:10.1021/acs.orglett.8b00831

Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane

Chang Hee Lee, Soo Min Lee, Byul Hana Min, Dong Su Kim, Chul Ho Jun

Department of Chemistry

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

14 Citations (Scopus)

Abstract

A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl₃ as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.

Original language	English
Pages (from-to)	2468-2471
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.8b00831
Publication status	Published - 2018 Apr 20

Bibliographical note

Funding Information:
†Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea ‡New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea

Funding Information:
This work was supported by a grant from the National Research Foundation of Korea (NRF) (Grant 2016-R-1-A2b4009460).

Publisher Copyright:
© 2018 American Chemical Society.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane",

abstract = "A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.",

author = "Lee, {Chang Hee} and Lee, {Soo Min} and Min, {Byul Hana} and Kim, {Dong Su} and Jun, {Chul Ho}",

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AU - Lee, Chang Hee

AU - Lee, Soo Min

AU - Min, Byul Hana

AU - Kim, Dong Su

AU - Jun, Chul Ho

N1 - Funding Information: †Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea ‡New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea Funding Information: This work was supported by a grant from the National Research Foundation of Korea (NRF) (Grant 2016-R-1-A2b4009460). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/4/20

Y1 - 2018/4/20

N2 - A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.

AB - A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.

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Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane

Abstract

Bibliographical note

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