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Physical Data: mp -22 °C; bp 105-106 °C; d 1.418 g cm-3.
Solubility: sol ether, acetone, and methylene chloride.
Handling, Storage, and Precautions: is corrosive and moisture sensitive. It should be used in an anhydrous atmosphere. Pure ClCH2COCl can be obtained by simple distillation of the commercial product. This reagent should be used in a fume hood.
Chloroacetyl chloride is a versatile reagent and has been extensively used in organic synthesis. It is primarily used as an acylating agent. The multi-functional nature of ClCH2COCl has made it a suitable two-carbon building block for cyclization. Numerous cyclic compounds, especially heterocycles, have been prepared through the use of the reagent. Chloroacetyl chloride is also a valuable precursor for monochloroketene and occasionally serves as a chlorinating agent.
In the Friedel-Crafts reaction, both the acyl and the alkyl chloride functionalities of ClCH2COCl can react with an arene, resulting in the formation of a cyclic compound. For example, treatment of 1,2,3,4-tetrahydronaphthacene with ClCH2COCl/AlCl3 led to formation of 6-oxo-1,2,3,4,5,6-hexahydrobenz[d]aceanthrylene in 22% yield (eq 3).6a When 3,5-dimethoxytoluene is used as the substrate, a 2,3-dihydrobenzofuran-3-one is obtained almost quantitatively (eq 4).6b,c The carbonyl group of ClCH2COCl may also participate in cyclization under appropriate conditions.6d,e This behavior is illustrated by the formation of 2,7-difluoro-9-chloromethylenexanthene in the reaction of 4,4�-difluorophenyl ether with ClCH2COCl under AlCl3 activation (eq 5).
Similar to C-acylation, cyclocondensation can also proceed in N-acylation to form cyclic compounds.25 The a-chlorine atom of ClCH2COCl is also reactive in this case.
The cyclization is not limited to the formation of only C-N and C-C bonds, but can also occur through forming C-N and C-N bonds.26 This transformation was exemplified by the preparation of 3-hydroxy-1-phenylpyrido[1,2-a]pyrazinium chloride in the reaction of ClCH2COCl with phenyl(2-pyridyl)ketimine (eq 12).26b Besides the a-chlorine, the carbonyl group of ClCH2COCl can also be utilized for the cyclization.
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