Concise trichlorination of methyl ketones using sodium hypochlorite pentahydrate
Abstract
We report a practical and efficient method for the synthesis of trichloromethyl ketones from the corresponding methyl ketones via a two-step sequence involving trifluoroacetylation followed by selective chlorination. The key chlorination step proceeds under mild, weakly acidic conditions using sodium hypochlorite pentahydrate, thus avoiding the use of hazardous chlorine gas or strong bases. A wide range of aromatic and aliphatic methyl ketones was successfully converted into the corresponding trichloromethyl ketones in high yields. Mechanistic studies suggest that the reaction involves the formation of a 2,2-dichloro-1,3-diketone intermediate and subsequent cleavage of the trifluoroacetyl group. In contrast to previously reported base-mediated halogenation methods, the present protocol exhibits a high regioselectivity and operational simplicity under acidic conditions. This method provides a convenient alternative for the synthesis of trichloromethyl ketones from readily available substrates and is expected to be broadly applicable in organic synthesis and medicinal chemistry.
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BibTeX
@article{sakai2026concise,
title = {{Concise trichlorination of methyl ketones using sodium hypochlorite pentahydrate}},
author = {Ayumu Sakai and Takumi Tanaka and Takahiro Hosokawa and Takumi Kawai and Hideyuki Tsutsui and Yoshikazu Kimura and Shinobu Takizawa and Masayuki Kirihara},
journal = {Beilstein Journal of Organic Chemistry},
year = {2026},
month = oct,
doi = {10.3762/bjoc.22.113},
url = {https://www.beilstein-journals.org/bjoc/articles/22/113},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Concise trichlorination of methyl ketones using sodium hypochlorite pentahydrate
AU - Ayumu Sakai
AU - Takumi Tanaka
AU - Takahiro Hosokawa
AU - Takumi Kawai
AU - Hideyuki Tsutsui
AU - Yoshikazu Kimura
AU - Shinobu Takizawa
AU - Masayuki Kirihara
PY - 2026
DA - 2026/10/08
JO - Beilstein Journal of Organic Chemistry
DO - 10.3762/bjoc.22.113
UR - https://www.beilstein-journals.org/bjoc/articles/22/113
AB - We report a practical and efficient method for the synthesis of trichloromethyl ketones from the corresponding methyl ketones via a two-step sequence involving trifluoroacetylation followed by selective chlorination. The key chlorination step proceeds under mild, weakly acidic conditions using sodium hypochlorite pentahydrate, thus avoiding the use of hazardous chlorine gas or strong bases. A wide range of aromatic and aliphatic methyl ketones was successfully converted into the corresponding trichloromethyl ketones in high yields. Mechanistic studies suggest that the reaction involves the formation of a 2,2-dichloro-1,3-diketone intermediate and subsequent cleavage of the trifluoroacetyl group. In contrast to previously reported base-mediated halogenation methods, the present protocol exhibits a high regioselectivity and operational simplicity under acidic conditions. This method provides a convenient alternative for the synthesis of trichloromethyl ketones from readily available substrates and is expected to be broadly applicable in organic synthesis and medicinal chemistry.
SN - 1860-5397
ER -