85630-30-4

Upstream product

• 85630-17-7 3-methoxyphenyl N,N-diethylcarbamate 
• 150-19-6 O-methylresorcine 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 154045-69-9 1,2-dimethoxy-3-(methoxymethoxy)benzene 
• 154045-68-8 N,N-diethyl-2-methoxy-6-(methoxymethoxy)benzamide 
• 51674-10-3 N,N-diethyl-2-methoxybenzamide 

Downstream Products

• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 88430-97-1 N,N-diethyl-2-methoxy-6-methylbenzamide 
• 154045-66-6 2-diethylcarbamoyl-3-methoxyphenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Anionic snieckus-fries rearrangement: Solvent effects and role of mixed agregates

Lithiated aryl carbamates (ArLi) bearing methoxy or fluoro substituents in the meta position are generated from lithium diisopropylamide (LDA) in THF, n-BuOMe, Me2NEt, dimethoxyethane (DME), N,N,N′,N′- tetramethylethylenediamine (TMEDA), N,N,N′

Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Regioselectivity in the Reductive Cleavage of Pyrogallol Derivatives: Reductive Electrophilic Substitution of Acetals of 2,3-Dimethoxyphenol

Acetals of 2,3-dimethoxyphenol were used as the starting materials for the transformation of 1,2,3-trioxygenated benzenes into various 1-oxygenated-2,3-dicarbon-substituted benzenes, via regioselective reductive electrophilic substitution of the 2-methoxy

Reductive Electrophilic Substitution of Pyrogallol Derivatives: Synthesis of 2,3-Disubstituted Phenols

1,2-Dimethoxy-3-methoxymethoxybenzene, 1, was used as the starting material for the transformation of a 1,2,3-trioxybenzene into various 1-oxy-2,3-dicarbobenzenes, via regioselective reductive electrophilic substitution of the 2-methoxy group followed by

Directed ortho metalation of n,n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri- and tetra-substituted oxygenated aromatics, phthalides and phthalic anhydrides

Full experimental details for the directed ortho metalation approch to a variety of simple ortho-substituted N,N-diethyl benzamides (Table 1) and contiguously 1,2,3- and 1,2,3,4-substituted benzamides (Tables 2) are given. The efficient conversion of these benzamides (6, 10, 12, 13, 18, 19) into phthalides (9a-b, 16b-c, 17) and phthalic anhydrides (8,16a), compounds previously available by demanding, classical methods, is detailed. A short synthesis of iso-ochracinic acid (27) is described.

The Directed Ortho Lithiation of O-Aryl Carbamates. An Anionic Equivalent of the Fries Rearrangement

Ortho-Lithiated O-aryl carbamates 3 constitute new synthetic intermediates which by treatment with a variety of electrophiles lead to ortho-substituted carbamates 4 and by rearrangement provide salicylamides 6.