2178-24-7

Usage

Uses

ETHYL 2-(2-BROMOPHENYL)ACETATE is a useful research chemical.

InChI:InChI=1/C10H11BrO2/c1-2-13-10(12)7-8-5-3-4-6-9(8)11/h3-6H,2,7H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 7154-66-7 2-bromobenzoic acid chloride 
• 64-17-5 ethanol 
• 71740-65-3 1-Bromo-2-((Z)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-benzene 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 150-46-9 triethyl borate 
• 201230-82-2 carbon monoxide 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 18698-97-0 ortho-bromophenylacetic acid 
• 860190-08-5 3-(2-bromo-phenyl)-2-thioxo-propionic acid 
• 7664-93-9 sulfuric acid 
• 101-97-3 Ethyl 2-phenylethanoate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 244205-40-1 (2-bromophenyl)boronic acid 

Downstream Products

• 78024-77-8 diethyl (2-bromophenyl)malonate 
• 113642-03-8 ethyl (o-bromophenyl)acetate ketene trimethylsilyl acetal 
• 75554-14-2 2,4-di(2-bromophenyl)-3-oxobutanenitrile 
• 910661-37-9 ethyl 2-[2-(3-oxobutyl)phenyl]ethanoate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 907584-58-1 ethyl (o-bromophenyl)-(4-oxoazetidin-2-yl)acetate 
• 150478-22-1 4-(α-ethoxycarbonyl-benzyloxy)benzyl alcohol 
• 150478-89-0 2-n-Butyl-1-[4-[(α-ethoxycarbonyl)benzylamino]-benzyl]benzimidazole 
• 1074-16-4 2-bromophenylethyl alcohol 
• 1035815-66-7 ethyl (E)-1-phenyl-2-cyano-cyclopropanecarboxylate 
• 4895-92-5 ethyl phenanthrene-9-carboxylate 
• 232611-22-2 9-ethyl 10-methylphenanthrene-9-carboxylate 
• 1189770-74-8 C₁₆H₁₇NO₃ 
• 90798-47-3 ethyl α-bromo-α-(2-bromophenyl)acetate 

Relevant academic research and scientific papers

Borylation of Unactivated C(sp3)-H Bonds with Bromide as a Traceless Directing Group

A palladium-catalyzed alkyl C-H borylation with bromide as a traceless directing group is described, providing a convenient approach to access alkyl boronates bearing a β-all-carbon quaternary stereocenter. The protocol features a broad substrate scope, excellent site selectivity, and good functional group tolerance.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Customized Buchwald-Type Phosphines Bearing an "Inverted" Pyrimidinium Betaine as an Aryl Group Surrogate - Synthesis and Coordination Chemistry with Gold(I)

A new ligand scaffold inspired by Buchwald-type phosphines is disclosed. Its design consists of the formal replacement of the distal aryl group of the original archetype by a pyrimidinium betaine connected to the o-phosphinophenyl moiety through the C-5 position of its malonate subunit. A productive synthetic pathway towards this phosphine is described along with its ability to coordinate to a gold(I) center. A weak bonding interaction between the metal center and the malonate group is observed in the solid state.

One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives

A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

A chemoselective Reformatsky-Negishi approach to α-haloaryl esters

A practical synthesis of α-haloaryl esters has been achieved via a chemoselective Negishi coupling of poly-halogenated aromatics and Reformatsky reagents in the presence of catalytic Pd(dba)2 and Xantphos. This chemistry tolerates a variety of aryl halides and was successfully applied to the synthesis of Ibuprofen. The α-haloaryl ester products, exemplified by ethyl 2-(4-bromo-2-chlorophenyl)acetate (3a), can be further functionalized via palladium or copper catalysis to afford an array of α-aryl esters.

Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities

It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright

COMPOUNDS FOR THE TREATMENT OF CNS DISORDERS

The invention relates to novel cycloalkyl- or cycloalkenyl-substituted pyrazolopyrimidinones of formula (I), wherein ā is selected from the group A1 consisting of a C3-C8-cycloalkyl group or a C4-C8-cycloalkenyl group, whereby the members of C3-C8-cycloalkyl group being selected from the group of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptanyl and cyclooctanyl; and the members of the C4-C8-cycloalkenyl group, being selected from cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cycloheptatrienyl, cyclooctathenyl, cyclooctatetraenyl. The new compounds shall be used for the manufacture of medicaments, in particular medicaments for improving perception, concentration, learning and/or memory in patients in need thereof. Chemically, the compounds are characterised as pyrazolopyrimidinones with a cycloalkyl-moiety directly bound to the 1 position of the pyrazolopyrimidinone and a second substituent in the 6 position which is bound via an optionally substituted methylene-bridge. Further aspects of the present invention refer to a process for the manufacture of the compounds and their use for producing medicaments.

Discovery and optimization of a biphenylacetic acid series of prostaglandin D2 receptor DP2 antagonists with efficacy in a murine model of allergic rhinitis

Biphenylacetic acid (5) was identified through a library screen as an inhibitor of the prostaglandin D2 receptor DP2 (CRTH2). Optimization for potency and pharmacokinetic properties led to a series of selective CRTH2 antagonists. Compounds demonstrated potency in a human DP2 binding assay and a human whole blood eosinophil shape change assay, as well as good oral bioavailability in rat and dog, and efficacy in a mouse model of allergic rhinitis following oral dosing.

BIPHENYLACETAMIDE DERIVATIVE

The present invention provides a compound of formula (I) or a salt thereof, wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, bromine atom, C1-6 alkyl, C1-6 alkoxy substituted with fluorine atom, and others; R4 and R5 are independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, C1-6 alkyl, C1-6 alkoxy substituted with fluorine atom, and others; R6 and R7 are independently selected from the group consisting of hydrogen atom, fluorine atom, methyl, ethyl, hydroxy group, and others; and R8 and R9 are independently selected from the group consisting of hydrogen atom, C1-6 alkyl, and others, which is useful as an agent for treating or preventing various types of epilepsy including partial seizures and/or generalized seizures.