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Synlett 2010(5): 835-836  
DOI: 10.1055/s-0029-1219387
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© Georg Thieme Verlag Stuttgart ˙ New York

Chloroacetylchloride: A Versatile Reagent in Heterocyclic Synthesis

Ramesh Yella*
Department of Chemistry, Indian Institute of Technology Guwahati, 781 039 Guwahati, India
e-Mail: ramesh@iitg.ernet.in;
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Publication History

Publication Date:
23 February 2010 (online)

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Introduction

Chloroacetylchloride is widely used in organic synthesis as a bifunctional reagent because acyl chloride (hard electrophile) easily forms esters [¹] or amides, [²-4] while the other end the chloromethyl site (soft electrophile) can form other linkages. [²-7] It is a convenient reagent for the preparation of heterocyclic compounds and is utilized as an important building block in the synthesis of natural and therapeutically active compounds. [¹0] [¹¹]

The reagent is used in the preparation of alachlor, butachlor, and the local anesthetic and antiarrhythmic drug lidocaine. [¹²] Furthermore, it is also used to produce phenacyl chloride, another chemical intermediate used as a tear gas via Friedel-Crafts acylation of benzene using AlCl3 as catalyst. [¹³] Chloroacetylchloride must be handled with precaution because it reacts readily with nucleophiles, such as amines, alcohols, and water generating hydrochloric acid, making it a lachrymator.