when 6-bromonicotinonitrile (3c) reacted with KI in the EtOHmedium (entry 3). The reaction of 5-fluoro-2-bromopyridine (3d)with KI proceeded smoothly to produce the desired product,5-fluoro-2-iodopyridine (4d), in a yield of 87% (entry 5). Thereaction of 6-bromopyridin-3-amine 3e, which bears an electron-donating group NH2on the 3-position also proceeded smoothlyto produce the corresponding iodinated product 4e in a satisfac-tory yield (entry 5, 92% yield). Compared with 2-bromopyridine(3a), 3-bromothiophene (3f) exhibited the same good reactiv-ity in this type of halogen exchange reaction. 3-Iodothiophene(4f) was obtained in 88% yield (entry 6). Finally, the reaction of3-bromoquinoline (3g) was investigated under the same condi-tions. The Cu(I)-catalyzed halogen exchange reaction of 3g withFig