459-56-3

Basic information

• Product Name: 4-Fluorobenzyl alcohol
• Synonyms: LABOTEST-BB LT02003779;4-FLUOROBENZYL ALCOHOL;RARECHEM AL BD 0076;P-FLUOROBENZYL ALCOHOL;(4-Fluorophenyl)methanol;(4-Fluoro-phenyl)-methanol;4-Fluoro-benzenemethanol;Benzenemethanol, 4-fluoro-
• CAS NO: 459-56-3
• Molecular Formula: C₇H₇FO
• Molecular Weight: 126.13
• EINECS: 207-292-0
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;Alcohol;Fluorobenzene;Alcohols;Fluorine Compounds;C7 to C8;Oxygen Compounds;Aryl Fluorinated Building Blocks;Building Blocks;C7 to C8;C7-C8;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Oxygen Compounds
• Mol File: 459-56-3.mol
• Article Data: 234

Chemical Properties

• Melting Point: 23°C
• Boiling Point: 204-206 °C
• Flash Point: 194 °F
• Appearance: colorless or slightly yellow liquid
• Density: 1.156 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.828mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 14.29±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 1446930
• CAS DataBase Reference: 4-Fluorobenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorobenzyl alcohol(459-56-3)
• EPA Substance Registry System: 4-Fluorobenzyl alcohol(459-56-3)

Safety Data

• Hazard Codes: Xi,C
• Statements: 14-34-36/37
• Safety Statements: 23-24/25-45-36/37/39-27-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 459-56-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

4-Fluorobenzyl Alcohol has been used in the preparation of many compounds including amides.

InChI:InChI=1/C7H5FO/c8-7-3-1-6(5-9)2-4-7/h1-5H

Synthetic route

4-Fluorobenzoic acid (456-22-4) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	100%
Stage #1: 4-Fluorobenzoic acid With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Inert atmosphere; Stage #2: With silica gel In methanol at 50℃; for 3h;	90%
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 100℃; under 60006 Torr; for 22h;	84%

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With C24H30Cl2NPRuS2; potassium tert-butylate; hydrogen In dichloromethane; toluene at 80℃; under 15001.5 Torr; for 5h; Autoclave;	100%
With C55H44O2P4Ru; hydrogen In toluene at 80℃; under 38002.6 Torr; for 18h; Glovebox; Autoclave;	99%

p-fluorotoluene (352-32-9) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With cerium(IV) triflate; water at 20℃; for 25h;	100%
With sodium anthraquinone-2-sulfonate; oxygen In water at 30℃; Irradiation;

p-fluorobenzyl acetate (502-00-1) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With methanol; potassium permanganate at 25℃; chemoselective reaction;	99%
With water In acetonitrile for 0.166667h; Quantum yield; Irradiation;

methyl 4-flurobenzoate (403-33-8) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With C23H29Cl2N2OPRuS; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Catalytic behavior; Time; Autoclave;	99%
With C27H35Cl2N2OPRuS; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 100℃; under 37503.8 Torr; for 2h; Catalytic behavior; Time; Autoclave;	99%
With C27H34Cl2NO2PRuS; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Catalytic behavior; Time; Autoclave;	98%

2-((4-fluorobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With silica gel In ethyl acetate; Petroleum ether	99%
With silica gel In methanol at 60℃; for 3h; Inert atmosphere;	92%
In methanol at 20℃; for 1h; Inert atmosphere; Glovebox;	92%

4-fluorobenzyl trifluoroacetate (139058-95-0) → 4-fluorobenzylic alcohol (459-56-3) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A n/a B 97%
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; triethylamine In toluene at 90℃; under 52505.3 Torr; for 17h; Inert atmosphere; Glovebox;

C13H13FOSi → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium hydroxide In water Schlenk technique; Inert atmosphere;	97%
With sodium hydroxide In water

(4-fluorobenzyloxy)trimethylsilane (14629-55-1) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With 1-butyl-3-methylimidazolium chloride at 20℃; for 0.66h;	95%
With 1,4-diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles In methanol at 20℃; for 0.0833333h;	90%

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium tetrahydroborate In methanol	95%

1-chloromethyl-4-fluorobenzene (352-11-4) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With iron(III) sulfate; water In toluene at 110℃; for 3h; Ionic liquid;	93%
With water; sodium carbonate
With sodium carbonate for 6h; Heating; Yield given;

4-fluoro-N,N-diphenylbenzamide (79606-49-8) → 4-fluorobenzylic alcohol (459-56-3) + diphenylamine (122-39-4)

Conditions	Yield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 3h; Catalytic behavior;	A n/a B 93%

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3) + tris(4-fluorobenzyl)amine (932724-63-5) + para-fluorobenzylamine (140-75-0) + benzylamine (100-46-9) + 1-(4-fluorophenyl)-N-[(4-fluorophenyl)methyl]methanamine (134227-41-1)

Conditions	Yield
With ammonia; hydrogen; Ni/C catalyst In water at 120℃; under 28502.9 - 33753.4 Torr; for 17.5h;	A 1.2% B 1.4% C 90.7% D 0.4% E 1.8%

4-fluorobenzoic acid ethyl ester (451-46-7) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With C33H29FeMnN2O3P; hydrogen; potassium carbonate In ethanol at 90℃; under 37503.8 Torr; for 16h; Catalytic behavior; Solvent; Pressure; Autoclave;	90%
With [(Rc,Sp)-N-2-picoIynyI-1-(-2-bis(4-methoxy-3,5-dimethlphenyl)phosphino)ferrocenylethylamine]-kN1-kN2-kP-tricarbonylmanganese(I) bromide; hydrogen; potassium carbonate In ethanol at 90℃; Solvent; Reagent/catalyst; Temperature; Autoclave;	90%
With potassium tert-butylate; C39H41FeMnN2O5P(1+)*Br(1-); 1-Methylnaphthalene In ethanol at 100℃; for 22h; Temperature; Inert atmosphere; Schlenk technique; Darkness;	77%
Multi-step reaction with 2 steps 1: lithium tert-butoxide / tetrahydrofuran / 0 - 20 °C 2: sodium hydroxide / water / 1 h / 20 °C View Scheme
With C41H46FeMnN3O5P(1+)*Br(1-); hydrogen; potassium carbonate In ethanol at 70℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature;	43.3 %Spectr.

4-Fluorobenzyl bromide (459-46-1) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With water In dimethyl sulfoxide at 50℃; for 24h; Schlenk technique;	87%
With water; dimethyl sulfoxide at 50℃; for 24h; Schlenk technique; Sealed tube;	87%
With water; potassium carbonate

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3) + 4-Fluorobenzoic acid (456-22-4)

Conditions	Yield
With sodium hydroxide In water at 25℃; for 3.5h; Cannizzaro Reaction;	A n/a B 86%
With potassium hydroxide
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.2h;	A 88 % Chromat. B 11 % Chromat.
Stage #1: 4-fluorobenzaldehyde In neat (no solvent) for 0.0333333h; Green chemistry; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃; for 0.00416667h; Reagent/catalyst; Cannizzaro Reaction; Microwave irradiation; Green chemistry;

tributyl[4-(hydroxymethyl)phenyl]tin → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With methanol; sodium triflate; sodium hydrogencarbonate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate); silver(l) oxide In acetone at 65℃; for 4h; Sealed vial; Inert atmosphere;	80%
With copper(II) bis(trifluoromethanesulfonate); tetrabutylammonium triphenyldifluorosilicate In acetonitrile at 23 - 60℃; for 3h; Sealed tube; regiospecific reaction;	60%

4-fluorobenzaldehyde p-toluenesulfonylhydrazone (210422-66-5) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With water; potassium carbonate at 130℃; for 0.166667h; Microwave irradiation;	80%

4-fluoro-1-iodobenzene (352-34-1) + carbon dioxide (124-38-9) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With methyldiphenylsilane; palladium on activated charcoal In water; acetonitrile at 80℃; under 7500.75 Torr; for 9h;	80%

2-(4-fluorophenyl)-1,3-oxathiolane → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 2h;	80%

(±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran (18539-44-1) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With 1,4-diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles In methanol at 20℃;	80%

lithium pyrrolide (20671-52-7) + 4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3) + (4-fluorophenyl)(1H-pyrrol-2-yl)methanone (13169-73-8) + 1-(4-fluorophenyl)pentan-1-ol (3913-55-1)

Conditions	Yield
Stage #1: lithium pyrrolide With zirconium(IV) chloride In tetrahydrofuran; cyclohexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran; cyclohexane at -78 - 20℃; Inert atmosphere; Stage #3: 4-fluorobenzaldehyde In tetrahydrofuran; cyclohexane at 20℃; for 48h; Inert atmosphere;	A 13% B 8% C 79%

Pd(C5H5N)(C13H8N2SO2C6H4NO2)(C6H4CH2OH) (1063716-63-1) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With Selectfluor In acetonitrile at 50℃; for 0.5h; Product distribution / selectivity;	78%

N,N-dimethyl-4-fluorobenzamide (24167-56-4) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 7h; Sealed tube;	76%

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3) + 2,2-bis(4-fluorophenyl)ethanol

Conditions	Yield
With zinc In water at 90 - 160℃; for 2h; Microwave irradiation; Green chemistry;	A 13% B 75%

p-Fluorophenylacetic acid (405-50-5) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium tetrahydroborate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; oxygen; caesium carbonate In dichloromethane at 40℃; for 40h; Irradiation;	75%

p-fluorobenzamide (824-75-9) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;	73%

4-fluorobenzaldehyde (459-57-4) + dibenzylamine (103-49-1) → 4-fluorobenzylic alcohol (459-56-3) + N,N-dibenzyl-1-(4-fluorophenyl)methanamine (359445-99-1)

Conditions	Yield
With sodium tetrahydroborate; carbon dioxide In tetrahydrofuran at 20℃; Solvent;	A 27% B 72%
With sodium tetrahydroborate; carbon dioxide In 1,4-dioxane at 20℃; Solvent; Reagent/catalyst;	A 54% B 35%

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3) + 1,2-bis(4-fluorophenyl)-1,2-ethanediol (24133-58-2)

Conditions	Yield
With triethylamine; 2-hydroxyethanethiol In acetonitrile for 23h; Irradiation;	A 70% B 18%
With lithium sulfate; sulfuric acid; trilithium citrate; lithium chloride In methanol; water Product distribution; Mechanism; Ambient temperature; electrolysis in membrane flow cell with Pb cathode at several pH and cathode potential;
With lithium sulfate; sulfuric acid; trilithium citrate; lithium chloride In methanol; water Ambient temperature; electrolysis in membrane flow cell with a Pb cathode;

4-fluorobenzylic alcohol (459-56-3) → 4-Fluorobenzyl bromide (459-46-1)

Conditions	Yield
With phosphorus tribromide In benzene at 20℃;	100%
With 1,1,1,2,2,2-hexamethyldisilane In chloroform for 2.5h; Reflux;	98%
With trimethylsilyl bromide In neat (no solvent) at 20℃; for 18h; Green chemistry; chemoselective reaction;	98%

4-fluorobenzylic alcohol (459-56-3) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;	100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 90℃; for 6h;	100%
With iron(III) chloride; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; oxygen; sodium nitrite In 1,2-dichloro-ethane at 50℃; under 3000.3 Torr; for 5h; Autoclave;	99%

4-fluorobenzylic alcohol (459-56-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(tert-butyldimethylsilyloxymethyl)-4-fluorobenzene (113984-76-2)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 25℃;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	99%

4-fluorobenzylic alcohol (459-56-3) → 4-Fluorobenzoic acid (456-22-4)

Conditions	Yield
With sodium hypochlorite; sodium hydrogencarbonate for 1.33333h;	100%
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;	97%
With oxygen at 120℃; for 10h; Green chemistry;	95%

4-fluorobenzylic alcohol (459-56-3) + acetic anhydride (108-24-7) → p-fluorobenzyl acetate (502-00-1)

Conditions	Yield
With thalium(III) chloride tetrahydrate at 20℃; for 0.0666667h;	99%
With polyvinylpolypyrrolidone-bound boron trifluoride In acetonitrile at 20℃; for 2h;	99%
With tribromomelamine In dichloromethane at 20℃; for 0.833333h; Green chemistry; chemoselective reaction;	99%

4-fluorobenzylic alcohol (459-56-3) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl(4-fluorobenzyl)dimethylsilane

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	99%

4-fluorobenzylic alcohol (459-56-3) → 4-fluorobenzonitrile (1194-02-1)

Conditions	Yield
Stage #1: 4-fluorobenzylic alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;	99%
Stage #1: 4-fluorobenzylic alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 1h; Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 2h; Reagent/catalyst;	99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 5h; Autoclave; High pressure;	99%

4-fluorobenzylic alcohol (459-56-3) + cis-Octadecenoic acid (112-80-1) → p-fluorobenzyl oleate

Conditions	Yield
at 75℃;	99%

4-fluorobenzylic alcohol (459-56-3) + 2-amino-benzenethiol (137-07-5) → 2-(4-fluorophenyl)-benzothiazole (1629-26-1)

Conditions	Yield
With potassium tert-butylate In toluene at 20 - 110℃; for 48h;	99%
With C15H20MnN2O3S(1+)*Br(1-); potassium hydroxide In neat (no solvent) at 140℃; Inert atmosphere; Green chemistry;	76%
With sodium t-butanolate In toluene at 120℃; for 24h; Schlenk technique; Sealed tube; Green chemistry;	37%

carbon disulfide (75-15-0) + 4-fluorobenzylic alcohol (459-56-3) → C8H6FOS2(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In diethyl ether at 20℃; for 12h;	99%

9H-fluorene (86-73-7) + 4-fluorobenzylic alcohol (459-56-3) → 9-(4-fluorobenzyl)-9H-fluorene

Conditions	Yield
With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere;	99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate In toluene at 120℃; for 18h; Inert atmosphere; Sealed tube;	90%

4-fluorobenzylic alcohol (459-56-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → (4-fluorobenzyloxy)trimethylsilane (14629-55-1)

Conditions	Yield
With Nafion SAC-13 at 20℃; for 0.0666667h;	98%
Stage #1: 1,1,1,3,3,3-hexamethyl-disilazane With C12H24KO6(1+)*Br3H(1-) In acetonitrile at 20℃; for 0.0166667h; Stage #2: 4-fluorobenzylic alcohol In acetonitrile at 20℃; for 0.116667h;	97%
With 1,4-diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles In neat (no solvent) at 20℃; for 0.666667h;	97%

4-fluorobenzylic alcohol (459-56-3) → 4-fluorobenzyl iodide (3831-29-6)

Conditions	Yield
With hydrogen iodide for 1h; Heating;	98%
With chloro-trimethyl-silane; sodium iodide In acetonitrile 0 deg C, 10 min then up to r.t., 1 h;	97%
With natural kaolinitic clay; sulfuric acid; potassium iodide In various solvent(s) for 0.0833333h; Irradiation; microwave;	82%
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; iodine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; under 22502.3 Torr; Autoclave; Schlenk technique;	78%
With potassium fluoride; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide; trifluoroacetic acid at 20℃; for 0.2h;	70%

4-fluorobenzylic alcohol (459-56-3) + 4-cyanophenol (767-00-0) → 4-((4'-fluoro)benzyloxy)benzonitrile (56442-14-9)

Conditions	Yield
With F-DEAD-2; bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine In tetrahydrofuran at 20℃; for 3h; Mitsunobu reaction;	98%
With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine Mitsunobu reaction;	95%
With bis(3-(perfluoro-t-butyloxy)propyl)diazodicarboxylate; bis-phenyl-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phosphine In tetrahydrofuran at 20℃; for 8h; Mitsunobu reaction; Inert atmosphere;	90%

4-β-isocyanate-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851166-94-4) + 4-fluorobenzylic alcohol (459-56-3) → 4-β-(4-fluorobenzyloxycarbonyl)amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (851167-14-1)

Conditions	Yield
In dichloromethane at 20℃;	98%

4-fluorobenzylic alcohol (459-56-3) + acetoacetic acid methyl ester (105-45-3) + urea (57-13-6) → 4-(4-fluorophenyl)-5-(methoxycarbonyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one (283593-12-4)

Conditions	Yield
at 80℃; for 0.75h;	98%
Stage #1: 4-fluorobenzylic alcohol With bismuth(III) nitrate In various solvent(s) at 50℃; for 0.0833333h; Stage #2: acetoacetic acid methyl ester; urea In various solvent(s) at 90℃;	88%

4-fluorobenzylic alcohol (459-56-3) → p-fluorobenzamide (824-75-9)

Conditions	Yield
With tert.-butylhydroperoxide; ammonia; oxygen In water; N,N-dimethyl-formamide at 80℃; under 1520.1 Torr; for 5h; Green chemistry;	98%
With tert.-butylhydroperoxide; tetraethylammonium iodide; ammonium bicarbonate In 1,2-dichloro-ethane at 70℃; for 22h;	77%
With tert.-butylhydroperoxide; ammonium hydroxide In water at 100℃; for 16h;	72%
Multi-step reaction with 2 steps 1: cesium carbonate; styrene / iridium pentamethylcyclopentadienyl dichloride dimer / toluene / 24 h / 111 °C 2: 117 mg / hydroxylamine hydrochloride / iridium pentamethylcyclopentadienyl dichloride dimer / toluene / 16 h / 111 °C View Scheme
With ammonium acetate; oxygen In tert-Amyl alcohol at 130℃; under 3800.26 Torr; for 18h; Reagent/catalyst; Autoclave;	61 %Chromat.

4-fluorobenzylic alcohol (459-56-3) + aniline (62-53-3) → N-(p-fluorobenzyl)aniline (83444-25-1)

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In 1,2,4-Trimethylbenzene at 160℃; for 15h; Inert atmosphere;	98%
With C55H43ClN5P2Ru(1+)*Cl(1-); potassium hydroxide In toluene at 140℃; for 2h; Sealed tube;	93%
With [(η5-pentamethylcyclopentadienyl)IrIIIbis-(κC-1,3-dimethylimidazol-2-ylidene)Cl]BF4; potassium tert-butylate In toluene at 80℃; for 12h;	92%

4-fluorobenzylic alcohol (459-56-3) + formic acid ethyl ester (109-94-4) → 4-fluorobenzyl formate (1146963-53-2)

Conditions	Yield
With tribromomelamine In neat (no solvent) at 20℃; for 0.733333h; Green chemistry; chemoselective reaction;	98%
With poly(4-vinylpyridinium tribromide) at 20℃; for 0.833333h; neat (no solvent);	91%
Stage #1: formic acid ethyl ester With sulfuric acid; silica gel at 20℃; Stage #2: 4-fluorobenzylic alcohol at 20℃; for 0.0833333h; chemoselective reaction;

piperidine (110-89-4) + 4-fluorobenzylic alcohol (459-56-3) → 4-fluorobenzylpiperidine (139592-92-0)

Conditions	Yield
With polystyrene supported triphenylphosphine ruthenium complex In toluene at 120℃; for 20h; Sealed tube; Flow reactor;	98%

5-bromo-2-fluoropyridine (766-11-0) + 4-fluorobenzylic alcohol (459-56-3) → 5-bromo-2-((4-fluorobenzyl)oxy)pyridine (936343-08-7)

Conditions	Yield
Stage #1: 4-fluorobenzylic alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	98%
Stage #1: 4-fluorobenzylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran; mineral oil at 0 - 80℃; for 3h;

4-fluorobenzylic alcohol (459-56-3) + acetic acid tert-butyl ester (540-88-5) → tert-butyl 3-(4-fluorophenyl)propanoate (1049037-23-1)

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; nickel diacetate In 1,4-dioxane; toluene at 100℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;	98%
With C22H34Cl2CoF3N5P2; potassium tert-butylate In toluene at 80℃; for 4h; Concentration; Inert atmosphere; Sealed tube; Glovebox;	82%
With Ru(η(2)-2-(2'-pyridyl)phenyl)Cl(CO)(PPh3)2; potassium tert-butylate In toluene at 80℃; for 1.5h; Inert atmosphere; Schlenk technique; Green chemistry;	82%
With C15H17ClIrNOP; potassium tert-butylate In toluene at 60℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;	79%

4-fluorobenzylic alcohol (459-56-3) + 1,1,1-trifluoro-2-isocyanatoethane (371-92-6) → 4-fluorobenzyl (2,2,2-trifluoroethyl)carbamate

Conditions	Yield
at 20℃;	98%

4-fluorobenzylic alcohol (459-56-3) + 3,5-dinitrobenzoic acid (99-34-3) → p-fluorobenzyl 3,5-dinitrobenzoate

Conditions	Yield
With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction;	97%
With PhP(C6H4-p-(CH2)2C6F13)2; bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)diazo dicarboxylate In tetrahydrofuran

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 64-17-5 ethanol 
• 459-57-4 4-fluorobenzaldehyde 
• 75-65-0 tert-butyl alcohol 
• 352-34-1 4-fluoro-1-iodobenzene 
• 124-38-9 carbon dioxide 
• 292638-85-8 acrylic acid methyl ester 
• 403-43-0 4-fluorobenzoyl chloride 
• 772-18-9 N-ethyl-4-fluorobenzamide 
• 502-00-1 p-fluorobenzyl acetate 
• 352-32-9 p-fluorotoluene 
• 13656-36-5 3,5-dichloro-2,4,6-trifluorobenzoic acid 
• 316142-60-6 N-(4-cyanophenyl)-4-fluorobenzamide 

Downstream Products

• 630413-23-9 1-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-2,5-dimethyl-1H-pyrrole 
• 214139-63-6 (4-fluorophenyl)methyl 2,2,2-trichloroethanimidate 
• 21469-80-7 trans-3-(4-fluorophenyl)-N,N-dimethylacrylamide 
• 1766-85-4 1-(4-fluorophenyl)-1-heptanone 
• 1032158-20-5 C₁₈H₁₃BrFNO₂ 
• 144084-37-7 O⁶-(4-fluorobenzyl)guanine 
• 456-22-4 4-Fluorobenzoic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 1020204-05-0 4'-fluorobenzyl β-D-glucopyranosiduronic acid 

Relevant articles and documents

A method of synthesis of alcohols

The present invention belongs to the field of organic synthesis technology, specifically a synthesis method of an alcohol; the present invention is under the catalytic action of tert-butanol lithium, with ester compounds and pinacol borane as raw materials, tetrahydrofuran as a solvent, reacted at 100 ° C for 24h, followed by adding 2mol / LNaOH / MeOH solution, stirred at room temperature overnight to obtain alcohol compounds; the raw materials of the present invention are of extensive sources or easy to prepare, the reaction conditions are relatively mild and do not require a large number of / cumbersome additives, in addition to the tert-butanol lithium catalyst is simple, And the prepared alcohol compounds are of high quality and high separation yield.

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