21218-94-0

Usage

Uses

Methyl 4-Phenoxybenzoate is useful for preparing potential InhA reductase inhibitors.

Synthesis Reference(s)

Tetrahedron, 43, p. 323, 1987 DOI: 10.1016/S0040-4020(01)89960-9

Upstream product

• 2215-77-2 4-Phenoxybenzoic acid 
• 67-56-1 methanol 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 3096-81-9 4-phenoxybenzonitrile 
• 108-86-1 bromobenzene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 108-95-2 phenol 
• 201230-82-2 carbon monoxide 
• 16307-38-3 (4-(methoxycarbonyl)phenyl)-λ³-iodanediyl diacetate 
• 619-44-3 methyl 4-iodobenzoate 
• 18052-27-2 tert-butyldimethyl(phenoxy)silane 
• 619-50-1 4-nitrobenzoic acid methyl ester 

Downstream Products

• 21120-75-2 methyl 4-(4-bromophenoxy)benzoate 
• 1592-38-7 2-Naphthalenemethanol 
• 2215-78-3 (4-phenoxyphenyl)methanol 
• 40501-41-5 methyl 4'-hydroxy-4-biphenylcarboxylate 
• 40501-40-4 methyl 2'-hydroxybiphenyl-4-carboxylate 
• 108-95-2 phenol 
• 855195-67-4 4-[4-(4-phenoxy-phenoxy)-phenoxy]-benzoic acid methyl ester 
• 143667-36-1 4-phenoxy-benzoic acid hydrazide 
• 2215-77-2 4-Phenoxybenzoic acid 
• 1382992-67-7 N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-phenoxybenzamide 
• 1612774-47-6 tert-butyl 3-(5-amino-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)-piperidine-1-carboxylate 
• 1612774-48-7 tert-butyl 3-(5-(tert-butoxycarbonylamino)-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1612777-08-8 tert-butyl 3-(5-(tert-butoxycarbonyl(methyl)amino)-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1612773-99-5 1-(1-acryloylpiperidin-3-yl)-5-(methylamino)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 

Relevant academic research and scientific papers

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer

Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

In vitro antimycobacterial activity and physicochemical characterization of diaryl ether triclosan analogues as potential inhA reductase inhibitors

Two sets of diphenyl ether derivatives incorporating five-membered 1,3,4-oxadiazoles, and their open-chain aryl hydrazone analogs were synthesized in good yields. Most of the synthesized compounds showed promising in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Three diphenyl ether derivatives, namely hydrazide 3, oxadiazole 4 and naphthylarylidene 8g exhibited pronounced activity with minimum inhibitory concentrations (MICs) of 0.61, 0.86 and 0.99 μg/mL, respectively compared to triclosan (10 μg/mL) and isoniazid (INH) (0.2 μg/mL). Compounds 3, 4, and 8g showed the InhA reductase enzyme inhibition with higher IC50 values (3.28-4.23 μM) in comparison to triclosan (1.10 μM). Correlation between calculated physicochemical parameters and biological activity has been discussed which justifies a strong correlation with respect to the inhibition of InhA reductase enzyme. Molecular modeling and drug-likeness studies showed good agreement with the obtained biological evaluation. The structural and experimental information concerning these three InhA inhibitors will likely contribute to the lead optimization of new antibiotics for M. tuberculosis.

Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers

Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal-free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (>30 examples) and the yields are high (52–95%, 80% avg.). One-pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity. (Figure presented.).

Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach

Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.

Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts

In this communication, an interesting phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts has been reported. At room temperature and under CO pressure, moderate to good yields of the desired esters can be produced in the absence of bases or an

Method for preparing ibrutinib

The invention discloses a method for preparing ibrutinib. The method includes the following steps of 1, preparation of IB-A, 2, preparation of IB-B, 3, preparation of IB-C, 4, preparation of IB-D, 5,preparation of IB-E, 6, preparation of IB-F, 7, preparation of IB-G, 8, preparation of IB-H, and 9, preparation of IB-J. The method has the advantages that the process is mature and stable, the quality of the product is stable, the production process is safe and reliable, and the ibrutinib is suitable for industrial production.

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.

Highly efficient heterogeneous copper-catalysed O-arylation of phenols by nitroarenes leading to diaryl ethers

The heterogeneous O-arylation of phenols by nitroarenes was achieved in DMF at 100 °C by using an MCM-41-immobilised bidentate nitrogen copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst, yielding a variety of unsymmetrical diaryl ethers in good to excellent yields. This heterogeneous copper catalyst can be easily prepared by a simple procedure from commercially readily available and inexpensive reagents, recovered by filtration of the reaction solution and recycled at least seven times without significant loss of activity.