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InChI:InChI=1/C8H6FNO/c1-5-10-7-3-2-6(9)4-8(7)11-5/h2-4H,1H3

Upstream product

• 53981-24-1 2-amino-5-fluorophenol 
• 78-39-7 Triethyl orthoacetate 
• 5078-07-9 6-hydroxy-2-methylbenzoxazole 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 75-36-5 acetyl chloride 
• 79-24-3 Nitroethane 
• 372-20-3 3-fluorophenol 
• 1247949-34-3 5-fluoro-2-(1-iminoethyl)phenol 
• 1445-45-0 Trimethyl orthoacetate 
• 446-36-6 5-fluoro-2-nitrophenol 

Downstream Products

• 1018467-26-9 3-[4-(carboxymethyl)benzyl]-6-fluoro-2-methyl-1,3-benzoxazol-3-ium bromide 

Relevant academic research and scientific papers

ANDROGEN RECEPTOR ANTAGONISTS

Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

Ligand-promoted, copper nanoparticles catalyzed one-pot synthesis of substituted benzoxazoles from 2-bromoanilines and acyl chlorides

A facile, highly efficient, and practical one-pot synthetic strategy for benzoxazoles was developed by using copper nanoparticles as a catalyst with o-bromoanilines and acyl chlorides as starting materials. With the promotion of 1,10-phenanthroline ligand, the copper nanoparticles catalyst showed highly catalytic activity under mild conditions. This methodology is tolerant of a wide variety of functional groups and gives good to excellent yields in most examples. Furthermore, the solid catalyst could be recovered and reused conveniently several times with satisfactory yields.

One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes

PPA-activated nitroalkanes are employed in the design of a one-pot cascade transformation involving metal-free and oxidant-free direct ortho-C-H functionalization, followed by Beckman rearrangement and intramolecular cyclocondensation to produce benzoxazoles and benzobisoxazoles directly from easily available phenols.

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds utilizing a novel organic reagent are described herein. The invention further discloses the utility of this reagent for incorporation of the 18 F isotope into hydroxyl group -containing organic molecules for PET imaging studies. Preparation of the reagents is described along with isolable intermediate structures from reaction of the reagent with a hydroxyl group-containing organic molecule.

PhenoFluorMix: Practical chemoselective deoxyfluorination of phenols

A practical deoxyfluorination with novel deoxyfluorinating reagent PhenoFluorMix, a mixture of N,N'-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF, is presented. PhenoFluorMix overcomes the challenges associated with hydrolysis of PhenoFluor. PhenoFluorMix does not hydrolyze, is readily available on decagram scale, and is storable in air. In this paper, we demonstrate the practicality of the reagent and exhibit the deoxyfluorination of a variety of phenols and heterocycles.

PhenoFluor: Practical synthesis, new formulation, and deoxyfluorination of heteroaromatics

We report a practical synthesis method of the reagent PhenoFluor on decagram scale, provide a new formulation of PhenoFluor as a toluene solution, which should decrease challenges associated with the moisture sensitivity of the reagent, and expand the substrate scope of deoxyfluorination with PhenoFluor to heteroaromatics.

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.

FLUORO-SUBSTITUTED BENZOXAZOLE POLYMETHINE DYES

Disclosed are reactive polyfluoro benzoxazole polymethine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which X is selected from the group consisting of -O-, -S- and at least one of groups