Synthesis of 2’,4‐Dibromo‐2,4’‐bithiazole Using Novel Long‐range Halogen Dance Reaction

Abstract

AbstractThis study presents a novel halogen dance reaction using 4,5‐dibromo‐2,4’‐bithiazole, which demonstrates a long‐range effect. The reaction involves the migration of a bromo group from the C5‐position to the C2’‐position of another thiazole ring when treated with lithium hexamethyldisilazide (LiHMDS), resulting in the formation of a non‐symmetric brominated bithiazole. In contrast, the base‐induced C2’‐bromination of 4‐bromobithiazole was found to be inefficient in synthesizing the desired brominated bithiazole due to its poor deprotonation selectivity.