One step conversion of tert-butyl ester to corresponding acyl chloride by thionyl chloride using water-free acetonitrile as solvent
A novel one-step protocol for the preparation of acyl chlorides directly from tert -butyl esters is described. The method employs anhydrous acetonitrile as the reaction medium and thionyl chloride (SOCl₂) as the chlorinating agent, facilitating the transformation under mild conditions to afford the target products in nearly quantitative yields. The reaction exhibits broad substrate scope, delivering excellent yields across a range of substrates. Notably, the simplicity, operational efficiency, and inherent safety of this procedure position it as a compelling alternative to existing methods for the synthesis of acyl chloride. A mechanism involving a Ritter-driven pathway is proposed to rationalize the conversion.
Authors
- Ailin Shan
- Shuai Song (ORCID: https://orcid.org/0000-0003-4353-2712)
- Xiaozhou Zhang (ORCID: https://orcid.org/0000-0002-7722-4630)
- Jiaqiang Cai
- Yaoxu Hong
- Zizhen Wang
- Lixia Zhang
- Tongtong Xue
Institutions
- Suzhou Research Institute (CN)
Publication Details
- Journal
- Tetrahedron Letters
- Published
- 2026-06-30
- DOI
- https://doi.org/10.1016/j.tetlet.2026.156195
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00