87453-28-9

Upstream product

• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 593-70-4 R₃₂ 
• 120-83-2 2,4-dichlorophenol 
• 533-23-3 ethyl 2,4-dichlorophenoxyacetate 

Relevant academic research and scientific papers

Molecular Structure and Crystal Packing of Monofluoromethoxyarenes

X-ray crystal structures of monofluoromethoxy aryl compounds are presented for the first time. In fluoromethoxybenzene derivatives with at least one unsubstituted ortho-position, the fluoromethoxy group adopts a twisted anisole conformation. The twist is

Continuous Heterogeneous Photocatalysis in Serial Micro-Batch Reactors

Solid reagents, leaching catalysts, and heterogeneous photocatalysts are commonly employed in batch processes but are ill-suited for continuous-flow chemistry. Heterogeneous catalysts for thermal reactions are typically used in packed-bed reactors, which cannot be penetrated by light and thus are not suitable for photocatalytic reactions involving solids. We demonstrate that serial micro-batch reactors (SMBRs) allow for the continuous utilization of solid materials together with liquids and gases in flow. This technology was utilized to develop selective and efficient fluorination reactions using a modified graphitic carbon nitride heterogeneous catalyst instead of costly homogeneous metal polypyridyl complexes. The merger of this inexpensive, recyclable catalyst and the SMBR approach enables sustainable and scalable photocatalysis.

Radical decarboxylative fluorination of aryloxyacetic acids using N-fluorobenzenesulfonimide and a photosensitizer

Fluorinated methoxy arenes are emerging as important motifs in both agrochemicals and pharmaceuticals. A novel technique for the synthesis of monofluoromethoxy arenes through the direct fluorodecarboxylation of carboxylic acids was developed that uses photosensitizers and N-fluorobenzenesulfonimide (NFSI). Utilization of the oxidatively mild fluorine transfer agent NFSI enabled the synthesis of fluoromethyl ethers that were previously inaccessible with decarboxylative fluorinations performed with Selectfluor. Mechanistic studies are consistent with the photosensitizer effecting oxidation of the aryloxyacetic acid.

Photo-fluorodecarboxylation of 2-aryloxy and 2-aryl carboxylic acids

Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron-poor 2-aryloxy and 2-aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single-electron transfer. Copyright

Electrophilic monofluoromethylation of O-, S-, and N-nucleophiles with chlorofluoromethane

CH2ClF has been found to be a useful electrophilic monofluoromethylating agent for a variety of O-, S-, and N-nucleophiles. The reaction is not sensitive to the radical scavenger such as nitrobenzene, which strongly supports an SN2 m

Facile Transformation of β-D-Ribofuranosyl Purines and Pyrimidines into Their Respective 3'-Deoxy-threo-pentofuranosyl Nucleosides

Practical syntheses of 3'-deoxy-β-D-threo-pentofuranosyl-uracil, -cytosine, -adenine, and -guanine (3U, C, A, G) from the corresponding ribonucleosides by two one-pot reactions with readily accessible reagents are described.The key reactions are the selective 3'-O-methanesulphonylations of the ribonucleosides, the deoxygenative -hydride shift of the methanesulphonates, and the reduction of in situ generated 3'-deoxy-2'-keto nucleosides therefrom.

Replecement of the carboxylic acid function with fluorine

Replacement of a carbonyl function by fluorine, fluorodecarboxylation, is a new process that can be accomplished by the reaction of alkanoic acids with xenon difluoride.Primary, tertiary, and benzylic acids perform best in the reaction, which is conducted at room temperature in methylene chloride or chloroform solution.A reaction mechanism is proposed in which the acid is initially converted to a fluoroxenon ester, RCO2XeF.The esters of the primary and secondary acids react by nucleophilic displacement by fluoride, as evidenced by incorporation of 18F- and no reactions common to free radicals or carbocations.The esters of the tertiary and benzylic acids react by converting to free radicals that can be further oxidized to carbocations.Thus incorporation of 18F- and racemization are observed with α-methoxy-α-trifluoromethylphenylacetic acid.Hydroxyl and amino functions inhibit the reaction.Aromatic and vinylic acids do not react.

Fluorodecarboxylation with Xenon Difluoride

The reaction between xenon difluoride and aliphatic carboxylic acids causes decarboxylation with replacement of the carboxyl group by fluorine.