Classifications

• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/20—Processes
  • C25B3/27—Halogenation
  • C25B3/28—Fluorination
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/01—Products
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/01—Products
  • C25B3/07—Oxygen containing compounds
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/01—Products
  • C25B3/09—Nitrogen containing compounds
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B3/00—Electrolytic production of organic compounds
  • C25B3/01—Products
  • C25B3/11—Halogen containing compounds

Definitions

• aliphatic hydrocarbyl (group) may be saturated or unsaturated.
• R′ represents a hydrogen atom, an alkyl group optionally having one or more substituents, an aralkyl group optionally having one or more substituents, an aryl group optionally having one or more substituents, an alkenyl group optionally having one or more substituents, a cycloalkyl group optionally having one or more substituents, a heterocycloalkyl group optionally having one or more substituents, a heterocyclic group optionally having one or more substituents, an alkoxy group optionally having one or more substituents, an aryloxy group optionally having one or more substituents, an amino group, a monoalkylamino group optionally having one or more substituents, a dialkylamino group optionally having one or more substituents, an acyl group, or an acylamino group); R 2 represents an alkyl group optionally having one or more substituents, an alkyl group optionally having one or more substituents, an alkyl group optionally having
• ketones include dialkyl ketones (e.g., acetone and methyl ethyl ketone), diketones (e.g., acetylacetone, acetoacetic acid, and acetoacetic acid esters), cycloalkanones (e.g., cyclohexanone), alkyl aryl ketones (e.g., acetophenone and propiophenone), diaryl ketones (e.g., benzophenone), 4-piperidone, 1-oxo-1,2-dihydronaphthalene, aryl(arylalkenyl)ketones (e.g., benzylideneacetophenone (chalcone)), aryl aralkyl ketones (e.g., deoxybenzoin), and ketals thereof, and the like.
• dialkyl ketones e.g., acetone and methyl ethyl ketone
• diketones e.g.
• any of the following reactions (2-3-1) to (2-3-5) is performed.
• reactions (2-3-1) to (2-3-4) one or more fluorine substituents are introduced into the aromatic moiety.
• fluorination of the aromatic ring of a phenol derivative or an aniline derivative can be carried out by fluorinating it and then reducing it with a reducing agent, such as zinc dust, to obtain the desired fluorinated compound.
• a phenol derivative forms, for example, the difluorinated quinonoid structure shown below, followed by reduction, thereby producing a phenol derivative having fluorine introduced at a position ortho or para to the hydroxyl group.
• R 5a , R 5b , R 5c , and R 5d are the same or different and each represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, a nitro group, a cyano group, a halogen atom, an alkanoyl group, an arylcarbonyl group, an amino group, a monoalkylamino group, a dialkylamino group, an alkanoylamino group, an arylcarbonylamino group, or an alkylthio group.
• R 5a , R 5b , R 5c , R 5d , R 5e , and R 5f are the same or different and each represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, a nitro group, a cyano group, a halogen atom, an alkanoyl group, an arylcarbonyl group, an amino group, a monoalkylamino group, a dialkylamino group, an alkanoylamino group, an arylcarbonylamino group, or an alkylthio group; and R 5g represents an alkyl group, an aralkyl group, an aryl group, an alkoxy group, a nitro group, a cyano group, a halogen atom, an alkanoyl group, an arylcarbonyl group, an amino group, a monoalkylamino group, a dialkylamino group, an al
• an aniline derivative forms, for example, the difluorinated quinonoid structure shown below, followed by reduction, thereby producing an aniline derivative having fluorine introduced at an ortho-positon or the para-position.
• aniline optionally having one or more substituents is used as an aniline derivative; however, it is also possible to introduce a fluorine atom into an aromatic ring when naphthylamine optionally having one or more substituents is used.
• Examples of (hetero)arylmethyl moiety-containing compounds include triarylmethanes (e.g., triphenylmethane), aryldialkylmethanes (e.g., 4-bromocumene), and arylacetic acid esters (e.g., ethyl (4-methoxyphenyl)acetate).
• triarylmethanes e.g., triphenylmethane
• aryldialkylmethanes e.g., 4-bromocumene
• arylacetic acid esters e.g., ethyl (4-methoxyphenyl)acetate
• thiocarbonyl compounds include O-aryl S-alkyl dithiocarbonates (e.g., O-(4-isopropylphenyl)S-methyl dithiocarbonate and O-(4-bromophenyl)S-methyl) dithiocarbonate), ((alkylthio)carbonothioyl)oxybenzoic acid esters (e.g., ethyl 4-(((methylthio)carbonothioyl)oxy)benzoate), O-alkyl S-alkyl dithiocarbonates (e.g., O-decyl S-methyl dithiocarbonate), O-aralkyl S-alkyl dithiocarbonates (e.g., O-(3-phenylpropyl)S-methyl) dithiocarbonate), O-alkyl cycloalkanecarbothioates (e.g., O-methyl cyclohexanecarbothioate), O-alkyl heteroarene
• formula (2) is R 1 —H, wherein R 1 is preferably a polyether group.
• formula (2) is R 1 —(SR 1a ) 2 , wherein R 1 is preferably
• the metal fluoride can function as a supporting salt (supporting electrolyte) in step A.
• fluoroalcohol examples include 2,2,3,3-tetrafluoro-1-propanol, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol, 2,2,3,3,3-pentafluoro-l-propanol.
• Preferred examples of the fluoroalcohol include 1,1,1,3,3,3-hexafluoro-2-propanol and 2,2,3,3,3-pentafluoro-1-propanol.
• the lower the upper limit of the temperature in step A the more likely it is that side reactions can be suppressed.
• the higher the lower limit of the temperature in step A the more likely it is that the progress of the desired reaction is promoted.
• metal fluoride is at least one metal fluoride selected from the group consisting of fluorides of metals belonging to Group 1 of the periodic table and fluorides of metals belonging to Group 2 of the periodic table.
• 1,1,1,3,3,3-Hexafluoro-2-propanol (2 mL), acetonitrile (8 mL), potassium fluoride (116 mg), and triphenylmethane (244 mg) were placed in a diaphragm-free cell with platinum plates connected thereto as electrodes, and constant-current electrolysis was performed at 5 mA/cm 2 under an air atmosphere at room temperature so that the total energization amount was 2 F/mol. After completion of the electrolysis, quantification by 19 F NMR revealed that the yield of fluorotriphenylmethane was 80%.
• 1,1,1,3,3,3-Hexafluoro-2-propanol (2 mL), nitromethane (8 mL), cesium fluoride (608 mg), and ethyl (phenylthio)acetate (196 mg) were placed in a diaphragm-free cell with platinum plates connected thereto as electrodes, and constant-current electrolysis was performed at 5 mA/cm 2 under an air atmosphere at room temperature so that the total energization amount was 2 F/mol.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Electrochemistry (AREA)
• Materials Engineering (AREA)
• Metallurgy (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Applications Claiming Priority (3)

Related Parent Applications (1)

Publications (1)

Family

ID=76788653

Family Applications (1)

Country Status (5)

Cited By (1)

Families Citing this family (2)

Citations (2)

Family Cites Families (1)

• 2021
  • 2021-01-08 EP EP21738342.1A patent/EP4089203A4/en active Pending
  • 2021-01-08 JP JP2021570113A patent/JP7394408B2/ja active Active
  • 2021-01-08 WO PCT/JP2021/000542 patent/WO2021141120A1/ja not_active Ceased
  • 2021-01-08 CN CN202180008374.6A patent/CN114945711A/zh active Pending
• 2022
  • 2022-07-07 US US17/859,462 patent/US20220341045A1/en active Pending

Patent Citations (2)

Also Published As

Similar Documents

Legal Events