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A four-component reaction for electrophilic chloro(ω-alkoxy)lation of alkenes has been described. The stable chloro-iodine(iii) reagent and SOCl2 were used as electrophilic and nucleophilic chlorine sources, respectively. This approach provides a straightforward way to synthesize various useful β-chloro ω-chloroalkyl ethers from a wide range of alkenes, including electron-deficient, aromatic and unactivated alkenes. The synthetic applications of this approach were also explored in some useful transformations.