71095-23-3

Usage

Uses

Used in Organic Synthesis:
1-(2′-bromo-5′-methoxyphenyl)ethan-1-ol is used as a building block in organic synthesis for its ability to form a variety of important compounds due to its unique structure.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(2′-bromo-5′-methoxyphenyl)ethan-1-ol is used as a key intermediate for the development of new pharmaceuticals, leveraging its chemical reactivity and structural diversity.
Used in Pharmaceutical Production:
1-(2′-bromo-5′-methoxyphenyl)ethan-1-ol is utilized in the production of pharmaceuticals, where its unique functional groups can be exploited to create drugs with specific therapeutic properties.
Used in Agrochemicals:
1-(2′-bromo-5′-methoxyphenyl)ethan-1-ol is also used in the agrochemical industry, potentially for the development of new pesticides or other agricultural chemicals that can enhance crop protection and yield.
Used in Fragrance Industry:
1-(2′-bromo-5′-methoxyphenyl)ethan-1-ol is employed in the fragrance industry, where its aromatic nature contributes to the creation of novel and complex scents for various applications, such as perfumes and scented products.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 150192-39-5 2-Bromo-5-methoxybenzyl alcohol 
• 676-58-4 methylmagnesium chloride 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 71095-17-5 1-Amino-2-(2-brom-5-methoxyphenyl)-propan-2-ol 
• 1350844-20-0 1-(5-methoxy-2-(pent-1-ynyl)phenyl)ethanone 
• 1354364-30-9 2-(2-bromo-5-methoxyphenyl)butan-2-ol 
• 1379534-81-2 [4-methoxy-2-(propen-2-yl)phenyl]pentamethyldisilane 
• 1379534-73-2 C₁₇H₂₈O₂Si₂ 
• 1401416-24-7 tert-butyl (2E)-3-{2-[1-(3-tert-butoxy-3-oxopropoxy)ethyl]-4-methoxyphenyl}acrylate 
• 1616667-68-5 ethyl (2E)-3-(2-bromo-5-methoxyphenyl)but-2-enoate 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 1203447-27-1 4-methoxy-2-(prop-1-en-2-yl)benzoic acid 
• 171512-97-3 1-bromo-4-methyloxy-2-(prop-1-en-2-yl)benzene 

Relevant academic research and scientific papers

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations

A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

Phosphine- and water-promoted pentannulative aldol reaction

Herein, an efficient metal-free intramolecular aldol reaction for the synthesis of an unusual class of cyclopentanoids is described. The reaction of α-substituted dienones tethered with ketones in the presence of tributylphosphine and water provided aldols. The role of water was realised to be crucial for this transformation. Furthermore, isotopic labeling experiments provided vital information about the reaction mechanism.

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis

A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Preparation of isoindolinones via a palladium-catalyzed diamination

A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.

Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones

A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C-PdII species using a strong oxidant, peroxide, which is generated in situ from a Pd(OAc)2/bpy/O2/HOAc catalytic system.

Substitution controlled functionalization of ortho -bromobenzylic alcohols via palladium catalysis: Synthesis of chromenes and indenols

An efficient domino Pd-catalyzed transformation of simple ortho-bromobenzyl tertiary alcohols to chromenes is presented. Their formation is believed to proceed via the formation of a five-membered palladacycle, which, in turn, involves in an intermolecular homocoupling with the second ortho- bromobenzyltertiary alcohol to yield the homo-biaryl bond followed by intramolecular C-O bond formation. Interestingly, when there is an allylic substituent on the benzylic carbon atom, a chemoselective switch was observed, which preferred intramolecular Heck coupling and gave indenols. Further, it has been confirmed that the tertiary alcohol functionality is indispensible to give the coupled products, whereas the use of primary/secondary benzylic alcohols furnished the simple carbonyl products via a possible reductive debromination followed by oxidation due to the availability of β-hydrogen(s).

Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H)- ones Dedicated to the memory of my teacher Professor P.V. Subba Rao, Department of Chemistry, Andhra University, Visakhapatnam

A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation.