An unexpected and direct synthesis of ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate (3) from the chlorotrimethylsilane (TMSCl)-promoted Friedländer reaction between 1-(2-amino-5-iodophenyl)ethanone (2) and ethyl 4-chloro-3-oxobutanoate has been disclosed. As a versatile and attractive building block, a synthetic application of the poly-functionalized quinoline 3 in the successive Williamson ether synthesis with various phenols and in situ ester hydrolysis reaction has been achieved and the corresponding 2,4-bis(aroxymethyl)quinoline-3-carboxylic acids (5a-k) were obtained in good yields of 71–86%.

中文翻译：

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2,4-双（氯甲基）-6-碘喹啉-3-羧酸乙酯的意外合成和应用

由氯三甲基硅烷（TMSCl）促进的1-（2-氨基-5-碘苯基）乙酮之间的Friedländer反应意外地直接合成2,4-双（氯甲基）-6-碘喹啉-3-羧酸乙酯（3）（2）和4-氯-3-氧代丁酸乙酯已被公开。作为一种多功能且有吸引力的构件，已经实现了多官能化喹啉3在随后的各种酚与威廉姆森醚合成中的合成应用以及原位酯水解反应，并获得了相应的2,4-双（芳氧基甲基）喹啉-3 -羧酸（5a-k）的收率为71–86％。