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• 40992-09-4 4-bromo-2-methoxy-5-methylphenol 
• 1195-09-1 5-methyl-2-methoxyphenol 

Relevant academic research and scientific papers

Synthesis of stable bromo-substituted masked o-benzoquinones and their application to the synthesis of bicyclo[2.2.2]octenones

Preparation of stable equivalents of some unstable masked o-benzoquinones and their use in the preparation of bicyclo[2.2.2]octenones is described.

Diels-Alder reactions of masked o-benzoquinones with acrylonitrile

Regioselective Diels-Alder reactions of masked o-benzoquinones (MOBs) 2a-i derived from the corresponding 2-methoxyphenols 1a-i with acrylonitrile leading to highly functionalized bicyclo[2.2.2]octenone derivatives in high yields are described.

A new and highly stereoselective approach to cis-clerodanes

A new and highly stereoselective approach to cis-clerodanes and its application to the synthesis of (±)-2 is described.

Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes

A rapid, efficient, and metal-free Lewis acid-mediated methodology has been developed for the site-selective synthesis of unsymmetrical oxygenated biaryls. This simple and efficient methodology furnished highly oxygenated and functionalized unsymmetrical biaryls in good to excellent yields by the direct oxidative coupling of electron-rich arenes to the α-position of carbonyl functionality of in situ generated masked benzoquinones.

Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective DielseAlder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration.

Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols

Intermolecular Diels-Alder reactions of masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5-7 and 21-24 generated from 2-methoxyphenols 1-3 and 17-20, respectively, with electron-deficient dienophiles leading to highly functionalized bicyclo[2.2.2]octenones are described. The masked o-benzoquinones (MOBs) 5-7 underwent Diels-Alder cycloadditions with methyl acrylate, methyl methacrylate, and methyl vinyl ketone to provide bicyclo[2.2.2]octenones 13a-c to 15a-c (direct method) in low to moderate yields with the concomitant formation of considerable amounts of dimers 9-11. To retard dimerization and to improve the yields of the requisite bicyclo[2.2.2]octenones, a detour method comprised of sequential bromination of 2-methoxyphenols 1-4, oxidation and Diels-Alder reaction, and debromination has been developed. The oxidation of bromophenols 17-20 produced MOBs 21-24 which are stable enough to be isolated. The MOBs 21-24 underwent cycloaddition with electron-deficient dienophiles in a very efficient manner to afford the corresponding cycloadducts 25a-c to 28a-c in good to high yields without self-dimerization. When the cycloadducts 25a-c to 28a-c were treated with either Bu3SnH/AIBN or tributylammonium formate-palladium reagent, the corresponding debrominated products 13a-c to 16a-c were obtained in high to excellent yields. In general, the cycloadducts 13a-c to 15a-c were obtained in 20-40% higher yields via the detour method than those via the direct method. In both routes, the Diels-Alder reactions proceeded in a highly regio- and stereoselective manner to furnish a single cycloadduct in each case.

Highly functionalized bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C60

The Diels-Alder reactions of masked obenzoquinones (MOBs) with [60]fullerene, affording novel and highly functionalized bicyclo[2.2.2]-octenone-fused [60]fullerene derivatives, are described.

One-pot stereoselective synthesis of tricyclic γ-lactones from 2-methoxyfuran and 2-methoxyphenols

A one-pot synthesis of the title compounds is achieved via highly facile Diels-Alder reactions of 2-methoxyfuran with masked o-benzoquinones.