115237-66-6

Upstream product

• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 108-95-2 phenol 

Downstream Products

• 1160707-99-2 N,N-diethyl-O-[2-(3-thienyl)phenyl]carbamate 
• 1245728-93-1 2-bromo-6-(trimethylsilyl)phenyl diethylcarbamate 
• 1445899-16-0 2-bromo-6-hydroxyphenyl diethylcarbamate 
• 1453186-28-1 (E)-methyl 3-(3-bromo-2-((diethylcarbamoyl)oxy)phenyl)acrylate 
• 211449-24-0 diethylcarbamic acid 2-acetylphenyl ester 
• 182489-46-9 Diethyl-carbamic acid 2-(1-diethylcarbamoyloxy-vinyl)-phenyl ester 

Relevant academic research and scientific papers

Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation

The directed ortho-lithiation reactions of O-aryl N,N-dialkylcarbamates as well as O-1-naphthyl and O-2-naphthyl N,N-dialkylcarbamates with sec-butyllithium/tetramethylethylenediamine (sBuLi/TMEDA) followed by quenching with various electrophiles afford a range of polysubstituted aromatic compounds. If the solutions of the ortho-lithiated carbamates are warmed to room temperature without the addition of external electrophiles, salicylamide and 1- and 2-hydroxynaphthamide derivatives are formed through anionic ortho-Fries rearrangements. The relative stabilities and reactivities of different O-aryl N,N-dialkylcarbamates were investigated. The lateral metalation of 2-tolyl carbamates with lithium diisopropylamide (LDA) provides a route to benzo[b]furan-2(3H)-ones. Previously reported results are used in a comparison of seven O-based directed metalation groups in reactions with several electrophiles. The described methodology is useful for the preparation of 1,2,3-substituted aromatic compounds.