628692-21-7

Usage

Uses

Used in Organic Synthesis:
2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is used as a building block in organic synthesis for the creation of complex organic molecules. Its boronic acid group allows for versatile reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is used as a key intermediate in the development of new drugs. Its unique reactivity and selectivity in organic reactions enable the synthesis of novel pharmaceutical compounds with potential therapeutic applications.
Used in Cross-Coupling Reactions:
2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is used as a reactant in cross-coupling reactions to introduce fluoro and methoxy functional groups into organic molecules. These reactions are essential for the synthesis of various organic compounds with specific properties and applications.
Used in Chemical Research:
In the field of chemical research, 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is used as a reagent to study the properties and reactions of organoboronic acid esters. Its unique reactivity and selectivity provide insights into the behavior of these compounds in various chemical processes.
Overall, 2-Fluoro-4-Methoxyphenylboronic acid pinacol ester is a versatile and valuable compound in the fields of organic synthesis, pharmaceutical research, and chemical studies, owing to its unique properties and reactivity.

Upstream product

• 458-50-4 1-bromo-2-fluoro-4-methoxybenzene 
• 73183-34-3 bis(pinacol)diborane 
• 456-49-5 1-fluoro-3-methoxybenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1214344-33-8 2-fluoro-4-methoxy-1-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities

Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp2)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-(iPrPNP)Co(H)2BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-(iPrPNP)Co(O2CtBu)2 (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen.

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectivel

A catalytic borylation/dehalogenation route to o -fluoro arylboronates

A two-step Ir-catalyzed borylation/Pd-catalyzed dehalogenation sequence allows for the net synthesis of fluoroarenes where the boronic ester is ortho to fluorine. Key elements of this approach include the use of a halogen para to the fluorine to block meta Ir-catalyzed borylation and the chemoselective Pd-catalyzed dehalogenation by KF activated polymethylhydrosiloxane (PMHS).

Transition metal-free synthesis of pinacol arylboronate: Regioselective boronation of 1,3-disubstituted benzenes

The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)-borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields. CSIRO 2014.

CETP INHIBITORS

Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. The compounds have 3 cyclic groups connected by single bonds, as for example triphenyl, which are attached directly to the ring of formula I or attached at the position B.