90359-76-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 70946-18-8 N,N-diethyl-3,4-dimethoxybenzamide 

Downstream Products

• 121424-97-3 N,N-diethyl-6-deuterio-3,4-dimethoxy-2-(trimethylsilyl)benzamide 
• 121425-14-7 N,N-diethyl-2-bromo-3,4-dimethoxybenzamide 
• 121425-17-0 N,N-diethyl-2,6-dibromo-3,4-dimethoxybenzamide 
• 121425-16-9 N,N-diethyl-6-bromo-3,4-dimethoxy-2-(trimethylsilyl)benzamide 
• 121424-98-4 N,N-diethyl-3,4-dimethoxy-6-formyl-2-(trimethylsilyl)benzamide 
• 113975-92-1 N,N-diethyl-4,5-dimethoxy-2-methyl-benzamide 
• 121425-07-8 N,N-diethyl-2-deuterio-4,5-dimethoxybenzamide 
• 130861-21-1 N,N-diethyl-6-methyl-4-(trimethylsilyl)-1,3-benzodioxole-5-carboxamide 
• 90359-81-2 N,N-diethyl-3,4-dimethoxy-6-methyl-2-(trimethylsilyl)benzamide 
• 73540-64-4 4,5-dimethoxy-3-phenylisobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Synthesis of pentasubstituted benzamides via orthometallation: Base and substituent effects

The synthesis of diversely substituted ori/io-methyl JV,./V-diethylbenzamides using the orthometallation concept is described. A dramatic effect of the substituents and the additive TMEDA is observed during metallation ortho to the N1N-diethylcarboxamido group. Molecular modeling confirms the conformational effect of substituents. A role for the TMEDA additive is proposed. Elscvier,.

Directed Ortho Metalation of N,N-Diethylbenzamides. Silicon Protection of Ortho Sites and the o-Methyl Group

New general methodology of value in aromatic chemistry based on silicon protection of preferred ortho metalation sites in benzamides and o-methyl groups in o-toluamides (1, 2, Scheme I) is described.According to these methodologies, routes (Scheme II and V) to 1,2,5-, 1,2,4,5-, and 1,2,3-substituted aromatics with a variety of functionalities and oxidation states have been developed (Tables I and II).These tactics are used for the synthesis of difficult to access halo (10a-b, Scheme III) and methyl (21,25, Scheme VI) heterocycles.Ipso bromodesilylation reactions with bromine lead regiospecifically to o-bromobenzamides (12a,c, 14, Scheme IV).Walk-around-the-ring metalation processes provide highly substituted aromatics 27, 28, 29, and 30 (Scheme VII); the X-ray structure of the hexasubstituted derivative 30 shows a significant puckering of the aromatic ring.Cesium fluoride induced carbodesilylation of o-silylbenzamides with benzaldehyde affords, after TsOH cyclization, phthalides (31a-c, Scheme VIII) and constitutes a neutral alternative to the directed ortho metalation approach. α- and α,α-silylated o-toluamides are used in fluoride-mediated carbodesilylation (34a,d, Scheme IX) and desilylative Peterson olefination (35, Scheme X) procedures, respectively.The utility of α-silylated o-toluamide for the synthesis of a tetralin (38, Scheme XI) via an o-quinodimethane species is given.