Introduction of a difluoromethylene group into organic compounds has been observed to impart them with positive properties, as viewed by a wide range of industries. Here, synthesis of 3,3-difluoro-2-pyrrolidone derivatives (7) was accomplished by the reaction of ethyl 2,2-difluoro-4-iodo-4-(trimethylsilyl) butanolate (4) with primary amines followed by desilylation. The key intermediate (4) was prepared from the addition reaction of trimethylvinylsilane (3) to ethyl difluoroiodoacetate (2) in the presence of Cu(0). Ethyl difluoroiodoacetate (2) was prepared starting from ethyl bromodifluoroacetate (1) via Reformatsky-type reaction.