In 2018,Angewandte Chemie, International Edition included an article by Ziegler, Dorothee S.; Karaghiosoff, Konstantin; Knochel, Paul. Synthetic Route of C4H9NO2. The article was titled 《Generation of Aryl and Heteroaryl Magnesium Reagents in Toluene by Br/Mg or Cl/Mg Exchange》. The information in the text is summarized as follows:
The alkylmagnesium alkoxide sBuMgOR·LiOR (R = 2-ethylhexyl), which was prepared as a 1.5M solution in toluene, undergoes very fast Br/Mg exchange with aryl and heteroaryl bromides, producing aryl and heteroaryl magnesium alkoxides (ArMgOR·LiOR) in toluene. These Grignard reagents react with a broad range of electrophiles, including aldehydes, ketones, allyl bromides, acyl chlorides, epoxides, and aziridines, in good yields. Remarkably, the related reagent sBu2Mg·2LiOR (R = 2-ethylhexyl) undergoes Cl/Mg exchange with various electron-rich aryl chlorides in toluene, producing diorganomagnesium species of type Ar2Mg·2LiOR, which react well with aldehydes and allyl bromides. In the experiment, the researchers used N-Methoxy-N-methylacetamide(cas: 78191-00-1Synthetic Route of C4H9NO2)
N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Synthetic Route of C4H9NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics