10.1002/ejoc.202100630
European Journal of Organic Chemistry
COMMUNICATION
Conclusions
Han, J. Chem. Res. 2019, 43, 205–210. (e) X. Wu, L. Zhou, R. Yang, F.
Guo, Z.-L. Tang, J. Xiao, J. Chem. Res. 2020, 44, 301–304.
In conclusion, we have successfully developed an iodine-
promoted direct conversion of inactivated amides and esters to
valuable acid chlorides in one-step. By using PCl3/I2 system, a
variety of substrates including aliphatic and aromatic amides and
esters could react with PCl3 to afford the corresponding products
in good yields. This protocol features of practical, simple and
easily scaled-up, providing not only a direct way for the
preparation of acid chlorides, but also insights for transformation
of amides and esters under metal-free conditions.
Experimental Section
Typical procedure for the chlorination of amides: Under air, a mixture of
amides 1 (1.3 mmol), PCl3, I2 and DMF in DCE (2.0 mL) was stirred in a
25 mL closed sealed tube in oil bath at indicated temperature for
indicated time. After the mixture was cooled down to the room
temperature, the solvent was evaporated under vacuum and distillation of
the residue under reduced pressure gave analytically pure acid chlorides
2.
Typical procedure for the chlorination of esters: Under air, a mixture of
esters 3 (1.3 mmol), PCl3 and I2 was stirred in a 25 mL closed sealed
tube in oil bath at indicated temperature for indicated time. After the
mixture was cooled down to the room temperature, the solvent was
evaporated under vacuum and distillation of the residue under reduced
pressure gave analytically pure acid chlorides 2.
Acknowledgments ((optional))
JX thanks financial support from National Natural Science
Foundation of China (21703061).
Keywords: phosphorus trichloride • chlorination• acid chlorides •
esters • amides
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