376396-10-0

Upstream product

• 67-56-1 methanol 
• 106-41-2 4-bromo-phenol 
• 7368-78-7 4-bromoguaiacol 

Downstream Products

• 1827620-20-1 C₇H₆BrClO₂ 
• 7368-78-7 4-bromoguaiacol 
• 557757-32-1 4-bromo-2,5-dimethoxyphenol 

Relevant academic research and scientific papers

Oxidation with hypervalent iodine reagents. Part II: Novel cyclohexadienones as precursors for the synthesis of anthraquinones

The oxidation of substituted phenols with phenyliodonium diacetate in methanol was found to afford 2,4-cyclohexadienones, 2,5-cyclohexadienones or mixtures of isomers, depending on the substrate being oxidized. Annulation of these cyclohexadienones with the anion of 3-cyanophthalide afforded anthraquinones in high yields.

A short and efficient route to novel scyphostatin analogues

Equation presented Several novel scyphostatin analogues have been prepared in up to 18% yield over five steps from commercially available 4-bromoguaiacol, utilizing an organometallic addition to afford the desired syn-hydroxy-epoxides.

Metal-free direct: C -arylation of 1,3-dicarbonyl compounds and ethyl cyanoacetate: A platform to access diverse arrays of meta -functionalized phenols

A base mediated, highly convenient strategy for the direct C-arylation of 1,3-dicarbonyls and cyanoacetate with various phenol derivatives as aryl partners is presented. The present work excels in forming a C-C bond at the meta-position of the phenols, which is traditionally challenging to functionalize. This protocol further leads the way to have scalable, straightforward access to phenol assimilated heterocycles which have powerful applications both in synthetic chemistry and medicinal research.

Lewis Acid Mediated [3+2] Coupling of Masked Benzoquinones with Styrenes: Facile Synthesis of 2,3-Dihydrobenzofurans

We have developed an efficient, simple, mild, and rapid method for the construction of dihydrobenzofuran derivatives by the [3+2] coupling of masked o-benzoquinones with styrene derivatives triggered by boron trifluoride diethyl etherate. This new [3+2] coupling protocol proceeds smoothly to afford dihydrobenzofuran derivatives in good to high yields within one minute. The method was extended to cycloaddition of p-benzoquinone monoketal with styrenes.

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.

Catalyst-Free Sulfonylation of 2-Methoxyphenols: Facile One-Pot Synthesis of (Arylsulfonyl)catechols in Aqueous Media

A new water-assisted carbon–sulfur bond-formation strategy is described for direct access to highly valuable (arylsulfonyl)catechols. This scalable transformation is remarkable, as a tandem dearomatization/sulfonylation and hydroxylation process enabled t

Unanticipated participation of HCl in nucleophilic chlorination reaction: Expedient route to meta chlorophenols

o-Quinone monoketals participated in a 1,4-addition reaction with HCl furnishing m-chlorophenols in high yields. Several readily available o-quinone monoketals were selected to display the generality of this serendipitous and unprecedented reaction and the results are presented herein.

Substituent effect on di-π-methane reactions of benzopyrazinobarrelenes and benzoquinoxalinobarrelenes

To examine the substituent effect on the di-π-methane (DPM) rearrangement of barrelene-like skeleton, benzopyrazinobarrelene (BPB) and benzoquinoxalinobarrelene (BQB) were utilized as the photoreaction experimental platforms. By the installation of the py

Diels-Alder reactions of 4-halo masked o-benzoquinones. Experimental and theoretical investigations

The studies on [4 + 2] cycloaddition of 4-halo derivatives of 6,6-dimethoxycyclohexa-2,4-dienones known as orthoquinone monoketals/masked o-benzoquinones are described. The 4-fluoro, 4-chloro- and 4-iodo-masked o-benzoquinones were stable enough for their

S-Arylation of thiols with masked o-benzoquinones: Synthesis of alkyl aryl/diaryl sulfides

A novel, efficient, and metal-free C-S bond formation of masked o-benzoquinones with thiols is reported. This protocol involves the synthesis of unsymmetrical alkyl aryl/diaryl sulfides in excellent yields under mild and catalyst-free conditions. This journal is