1583-58-0

Usage

Uses

Used in Organic Synthesis:
2,4-Difluorobenzoic acid is used as a synthetic building block for the creation of various organic compounds. Its unique molecular structure, featuring two fluorine atoms at the 2nd and 4th positions of the benzene ring, allows for specific reactivity and functional group manipulation in chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-difluorobenzoic acid is used as an intermediate for the development of new drugs. Its distinct chemical properties enable the creation of novel drug candidates with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
2,4-Difluorobenzoic acid is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique structure can contribute to the development of more effective and environmentally friendly products for agricultural use.
Used in Chemical Research:
In the field of chemical research, 2,4-difluorobenzoic acid serves as a model compound for studying various aspects of molecular conformation, vibrational and electronic transitions, and other fundamental chemical properties. This research can lead to a better understanding of molecular interactions and the development of new materials and applications.

InChI:InChI=1/C7H4F2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)/p-1

Synthetic route

2,4-difluoro-3-(triethylsilyl)benzoic acid (651027-06-4) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With potassium hydroxide In ethanol; water for 2h; Heating;	98%

N-(4-cyanophenyl)-2,4-difluorobenzamide → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With hydrogenchloride at 80℃; for 18h;	98%

2,4-difluoro-6-bromo-isopropylbenzene → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With 1,3-Dichloro-2-propanol; boron trifluoride diethyl etherate; water at 50℃; for 1.83333h; Temperature;	97%

carbon dioxide (124-38-9) + 2,4-difluoro-1-iodobenzene (2265-93-2) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -75℃;	92%
Stage #1: 2,4-difluoro-1-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran for 24h;	76%

2,4-difluorobenzonitrile (3939-09-1) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.5h; Green chemistry;	92%

2,4-difluoroethynylbenzene (302912-34-1) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h;	92%

2,4-difluoro-3-chlorobenzoic acid (154257-75-7) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With sodium hydroxide; zinc for 2h; Heating;	91%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 2,4-difluorophenyl 2,3,4,5,6-pentafluorobenzenesulfonate → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	90%

formic acid (64-18-6) + 2,4-difluoro-1-iodobenzene (2265-93-2) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	87%

2',4'-difluoroacetophenone (364-83-0) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic acid at 180℃; under 18751.9 Torr; for 1.5h; Reagent/catalyst; Temperature; Green chemistry;	85%
With sodium percarbonate; potassium tert-butylate; sphingosylphosphorylcholine; meta-dinitrobenzene In tert-butyl alcohol at 80℃; for 5h;	23%
With potassium permanganate Oxidation;

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 2,4-difluorophenyl trifluoromethanesulfonate → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	82%

2,4-dinitrobenzoic acid (610-30-0) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With potassium fluoride; cetyltrimethylammonim bromide In N,N-dimethyl-formamide at 120℃; for 7h;	72.4%

2,4-difluorotoluene (452-76-6) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With potassium permanganate

2,4-difluorobromobenzene (348-57-2) + carbon dioxide (124-38-9) → 3-bromo-2,6-difluorobenzoic acid (28314-81-0) + 2,4-difluoro-benzoic acid (1583-58-0) + 2,6-difluorobenzoic acid (385-00-2)

Conditions	Yield
With n-butyllithium 1) hexane, Et2O, 2 min, -78 deg C. 2) ether; Yield given. Multistep reaction. Yields of byproduct given;
With n-butyllithium 1) hexane, THF; 2 min, -78 deg C. 2) ether; Yield given. Multistep reaction. Yields of byproduct given;

4-Fluorobenzoic acid (456-22-4) → 2,3,4,5-tetrafluorobenzoic acid (1201-31-6) + 3,4-Difluorobenzoic acid (455-86-7) + 2,4,5-trifluorobenzoic acid (446-17-3) + 2,3,4,-trifluorobenzoic acid (61079-72-9) + 3,4,5-trifluorobenzoic acid (121602-93-5) + 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With fluorine In sulfuric acid Product distribution; various substrate to fluorine ratios; also in 98percent HCOOH;

2,4-difluorobenzaldehyde (1550-35-2) → 2,4-difluorophenol (367-27-1) + 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With 4-hydroxyacetophenone monooxygenase from P. fluorescens ACB; oxygen; NADPH In phosphate buffer at 30℃; for 1h; pH=8.0; Enzyme kinetics; Baeyer-Villiger oxidation;

1,3-Difluorobenzene (372-18-9) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BuLi / hexane; tetrahydrofuran / 0.75 h / -75 °C 1.2: 74 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: 90 percent / tetrahydrofuran; hexane 3.1: 91 percent / Zn; aq. NaOH / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 89 percent / butyllithium / hexane; tetrahydrofuran / -75 °C 2: 89 percent / sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h 3: 98 percent / potassium hydroxide / ethanol; H2O / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 98 percent / sec-BuLi; I2 / tetrahydrofuran; cyclohexane / -75 °C 2: 48 percent / LDA / tetrahydrofuran; hexane / -75 °C 3: 92 percent / BuLi / tetrahydrofuran; hexane / -75 °C View Scheme
Multi-step reaction with 2 steps 2: KMnO4 View Scheme

1-chloro-2,6-difluorobenzene (38361-37-4) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 90 percent / tetrahydrofuran; hexane 2.1: 91 percent / Zn; aq. NaOH / 2 h / Heating View Scheme

1-triethylsilyl-2,6-difluorobenzene (651027-02-0) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h 2: 98 percent / potassium hydroxide / ethanol; H2O / 2 h / Heating View Scheme

2,6-difluoroiodobenzene (13697-89-7) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / LDA / tetrahydrofuran; hexane / -75 °C 2: 92 percent / BuLi / tetrahydrofuran; hexane / -75 °C View Scheme

phenylhydrazine hydrochloride (59-88-1) + 2,4-difluorobenzoyl chloride (72482-64-5) → benzoic acid hydrazide (613-94-5) + 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
In pyridine	A 98 g (79%) B n/a

C22H18F2O4 → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
In ethanol; dichloromethane at 25℃; Kinetics;

2,4-difluorophenol (367-27-1) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; water / 16 h / 20 °C / Schlenk technique; Inert atmosphere View Scheme

2,4-difluorophenylcarbonylmethylenetriphenylphosphine → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;

2,4-dinitrotoluene (121-14-2) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Stage #1: 2,4-dinitrotoluene With ammonium chloride In ethanol at 75 - 85℃; for 1.16667h; Stage #2: With manganese(IV) oxide; tetrabutylammomium bromide; dihydrogen peroxide at 40 - 60℃; for 1h; Stage #3: With tetrabutylammomium bromide; sodium fluoride In N,N-dimethyl-formamide at 100 - 115℃; for 5.5h;

3,5-dichloro-N-(4-cyanophenyl)-2,4,6-trifluorobenzamide → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 2: hydrogenchloride / 18 h / 80 °C View Scheme

3,5-dichloro-2,4,6-trifluorobenzoyl chloride → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 3: hydrogenchloride / 18 h / 80 °C View Scheme

2,4,6-trifluoro-3,5-dichlorobenzoic acid (13656-36-5) → 2,4-difluoro-benzoic acid (1583-58-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 4 h / 70 °C 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; tris[2-phenylpyridinato-C2,N]iridium(III) / acetonitrile / 48 h / 60 °C / Sealed tube; Inert atmosphere; Photolysis 4: hydrogenchloride / 18 h / 80 °C View Scheme

2,4-difluoro-benzoic acid (1583-58-0) → 2,4-difluorobenzoyl chloride (72482-64-5)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Cooling with ice;	100%
Stage #1: 2,4-difluoro-benzoic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h;	100%
With thionyl chloride Heating;	96%

2,4-difluoro-benzoic acid (1583-58-0) → 2,4-difluoro-5-iodobenzoic acid

Conditions	Yield
With N-iodo-succinimide; sulfuric acid at 0℃; for 4h;	100%
With N-iodo-succinimide; trifluorormethanesulfonic acid at 5 - 50℃; for 1.5h; Product distribution / selectivity;	100%
With N-Iodosuccinamide; sulfuric acid at 0 - 5℃; for 5h;	94%

(2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-piperazin-1-ylpyrrolidine-1-carboxylic acid tert-butyl ester (869489-00-9) + 2,4-difluoro-benzoic acid (1583-58-0) → (2S,4S)-4-[4-(2,4-difluorobenzoyl)piperazin-1-yl]-2-(3,3-difluoropyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
Stage #1: (2S,4S)-2-(3,3-difluoropyrrolidine-1-carbonyl)-4-piperazin-1-ylpyrrolidine-1-carboxylic acid tert-butyl ester; 2,4-difluoro-benzoic acid With O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	100%

2,4-difluoro-benzoic acid (1583-58-0) → 2,4-difluoro-5-nitro-benzoic acid (153775-33-8)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 20℃; for 16.5h;	98%
With sulfuric acid; nitric acid In water at 20 - 50℃; for 3.5h;	98%
With sulfuric acid; nitric acid at 0 - 20℃; for 16.5h;	98%

3,4,5-Trimethoxyaniline (24313-88-0) + 2,4-difluoro-benzoic acid (1583-58-0) → 2,4-difluoro-N-(3,4,5-trimethoxyphenyl)benzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	98%

2,4-difluoro-benzoic acid (1583-58-0) → methyl 2,4-difluorobenzoate (106614-28-2)

Conditions	Yield
With thionyl chloride In methanol	97%
Multi-step reaction with 2 steps 1: thionyl chloride; sulfuric acid / 0.2 h / Inert atmosphere; Reflux 2: triethylamine / dichloromethane / 0 °C / Inert atmosphere View Scheme

2,4-difluoro-benzoic acid (1583-58-0) → 4-fluorosalicylic acid (345-29-9)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 130℃; for 4h;	95.1%
With sodium hydroxide In dimethyl sulfoxide at 130℃; for 8h;	90%
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 135℃; for 4h;	68%
With 1,3-dimethyl-2-imidazolidinone; sodium hydroxide at 135℃; for 6h;	67.52%
With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 150℃; for 1h;

benzo[1,3]dioxolo-5-ylamine (14268-66-7) + 2,4-difluoro-benzoic acid (1583-58-0) → N-(benzo[d][1,3]dioxol-5-yl)-2,4-difluorobenzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	93%

4-methoxy-aniline (104-94-9) + 2,4-difluoro-benzoic acid (1583-58-0) → 2,4-difluoro-N-(4-methoxyphenyl)benzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	93%

2,4-difluoro-benzoic acid (1583-58-0) → 3-fluorophenol (372-20-3)

Conditions	Yield
With water; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 170 - 175℃; for 15h; Sealed tube;	92.8%

3,4-dimethoxyaniline (6315-89-5) + 2,4-difluoro-benzoic acid (1583-58-0) → N-(3,4-dimethoxyphenyl)-2,4-difluorobenzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	91%

methyl (L)-leucinate hydrochloride (7517-19-3) + 2,4-difluoro-benzoic acid (1583-58-0) → (S)-methyl 2-(2,4-difluorobenzamido)-4-methylpentanoate

Conditions	Yield
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	90%

europium(III) hydroxide + 2,4-difluoro-benzoic acid (1583-58-0) → C21H13EuF6O8

Conditions	Yield
In methanol; acetone at 60℃; for 1h;	89%

tert-butyl alcohol (75-65-0) + 2,4-difluoro-benzoic acid (1583-58-0) → tert-butyl 2,4-difluorobenzoate (500353-15-1)

Conditions	Yield
With dmap; di-tert-butyl dicarbonate for 48h;	86%
With dmap; di-tert-butyl dicarbonate at 20℃; for 24h;	84%
With dmap; di-tert-butyl dicarbonate In dichloromethane at 20℃; for 24h;	84%

ethanol (64-17-5) + 2,4-difluoro-benzoic acid (1583-58-0) → ethyl 2,4-di-fluorobenzoate (108928-00-3)

Conditions	Yield
With sulfuric acid for 3h; Heating;	85%
With hydrogenchloride at 80℃; for 24.25h;	76%
Stage #1: ethanol; 2,4-difluoro-benzoic acid With hydrogenchloride for 5.33333h; Heating / reflux; Stage #2: With sodium hydroxide In diethyl ether; water
With hydrogenchloride
With sulfuric acid Heating;

3,5-dimethylphenyl iodide (22445-41-6) + 2,4-difluoro-benzoic acid (1583-58-0) → 3,5-difluoro-3',5'-dimethyl-1,1'-biphenyl (1344681-47-5)

Conditions	Yield
With palladium diacetate; acetic acid; silver carbonate at 130℃; for 16h; regioselective reaction;	85%

5-(3-fluoro-4-methoxyphenyl)-1H-pyrazole-3-carbohydrazide + 2,4-difluoro-benzoic acid (1583-58-0) → 2-(5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-3-yl)-5-(2,4-difluorophenyl)-1,3,4-oxadiazole

Conditions	Yield
With trichlorophosphate Reflux;	85%

ethyl 3-(dimethylamino)acrylate (924-99-2, 1117-37-9, 114894-59-6) + 2,4-difluoro-benzoic acid (1583-58-0) → (Z)-ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate

Conditions	Yield
Stage #1: 2,4-difluoro-benzoic acid With thionyl chloride at 80℃; for 2h; Stage #2: ethyl 3-(dimethylamino)acrylate With triethylamine In toluene at 90℃; for 12h;	85%

di-tert-butyl dicarbonate (24424-99-5) + tert-butyl alcohol (75-65-0) + 2,4-difluoro-benzoic acid (1583-58-0) → tert-butyl 2,4-difluorobenzoate (500353-15-1)

Conditions	Yield
dmap In dichloromethane at 20℃; for 24h;	84%

di-tert-butyl dicarbonate (24424-99-5) + 2,4-difluoro-benzoic acid (1583-58-0) → tert-butyl 2,4-difluorobenzoate (500353-15-1)

Conditions	Yield
With dmap In dichloromethane; tert-butyl alcohol at 20℃; for 24h;	84%
dmap In tert-butyl alcohol at 40℃; for 18h;	81%

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 364-83-0 2',4'-difluoroacetophenone 
• 124-38-9 carbon dioxide 
• 2265-93-2 2,4-difluoro-1-iodobenzene 
• 154257-75-7 2,4-difluoro-3-chlorobenzoic acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 72482-64-5 2,4-difluorobenzoyl chloride 
• 367-27-1 2,4-difluorophenol 
• 15226-74-1 dicobalt octacarbonyl 
• 264135-49-1 2,4-difluorophenyl trifluoromethanesulfonate 
• 64-18-6 formic acid 
• 13697-89-7 2,6-difluoroiodobenzene 
• 651027-02-0 1-triethylsilyl-2,6-difluorobenzene 
• 38361-37-4 1-chloro-2,6-difluorobenzene 

Downstream Products

• 52333-52-5 2-(2,4-difluoro-phenyl)-oxazolo[4,5-b]pyridine 
• 602-94-8 Pentafluorobenzoic acid 
• 161531-51-7 2,4-difluoro-5-iodobenzoic acid 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 446-17-3 2,4,5-trifluorobenzoic acid 
• 61079-72-9 2,3,4,-trifluorobenzoic acid 
• 153775-33-8 2,4-difluoro-5-nitro-benzoic acid 
• 330996-81-1 C₆₁H₇₉F₂NO₁₄Si₂ 
• 367955-15-5 {N-[3-(tert-Butoxycarbonylamino)propyl]-N-(2,4-difluorobenzoyl)amino}acetic acid tert-butyl ester 
• 28314-83-2 5-bromo-2,4-difluoro-benzoic acid 
• 865471-09-6 4-fluoro-2-(1-piperidinyl)benzoic acid 
• 85118-02-1 2,4-difluorobenzamide 
• 1045725-79-8 (S)-1-(2,4-Difluoro-benzoyl)-pyrrolidine-2-carboxylic acid 
• 79787-19-2 2,3-dihydro-5-(2,4-difluorophenyl)-6,7-bis(hydroxymethyl)-1H-pyrrolizine 

Relevant academic research and scientific papers

Hydrogen Bond Directed Photocatalytic Hydrodefluorination and Methods of Use Thereof

Methods of synthesizing compounds comprising fluorinated aryl groups are disclosed, wherein said methods utilize hydrogen bond directed photocatalytic hydrodefluorination.

Continuous synthesis method for substituted benzoic acid organic matter

The invention provides a continuous synthesis method for a substituted benzoic acid organic matter. The continuous synthesis method comprises the following steps: in the presence of a catalyst and anorganic solvent, continuously putting an organic matter of a formula (I) shown in the specification, and oxygen into a continuous reaction device, carrying out a continuous oxidation reaction so as toobtain the substituted benzoic acid organic matter, and continuously discharging the substituted benzoic acid organic matter, wherein the substituted benzoic acid organic matter is of a structure ofa formula (II) shown in the specification. Oxygen is a green reagent and is cheap and easy to obtain, a great amount of wastes are not generated after reactions are completed, and the system is easy to treat. Due to continuous reaction operation, the risk that the solvent has flash evaporation explosion because of high-concentration oxygen in in-batch reactions can be reduced. Under same oxidationconditions, due to a continuous preparation process, escape of oxygen can be reduced, the utilization rate of oxygen can be greatly increased, operation can be also simplified, the security of reactions can be improved, and the yield of the substituted benzoic acid organic matter can be increased.

Pharmaceutical intermediate 2,4-difluorobenzoic acid synthesis method

The invention discloses a pharmaceutical intermediate 2,4-difluorobenzoic acid synthesis method, which mainly comprises: adding 3-4 mol of a 1,3-dichloro-2-propanol solution, 2 mol of a 2,4-difluoro-6-bromo-isopropylbenzene solution and 600-800 ml of an aqueous solution to a reaction container, controlling the stirring speed at 110-130 rpm, heating the solution to a temperature of 40-50 DEG C, adding 5-6 mol of a boron trifluoride-butyl ether solution, maintaining for 90-110 min, carrying out pressure reducing concentration after completing the reaction, adding 300 ml of a 1-pentanol solution,filtering, adjusting the pH value of the filtrate to 4-5, crystallizing, filtering, re-crystallizing in a 4-methyl-2-pentanone solution, and dewatering with a dewatering agent to obtain the finishedproduct 2,4-difluorobenzoic acid.

Synthetic method of medical intermediate 2, 4-difluorobenzoic acid

The invention discloses a synthetic method of medical intermediate 2, 4-difluorobenzoic acid. The synthetic method specifically includes following steps: adopting a sol-gel method to prepare nano silicon oxide loaded Pd as a catalyst; adding cetyl trimethyl ammonium chloride to perform in-situ modification on the surface of the catalyst in the process of preparation; adding ammonium chloride and the prepared catalyst into the raw material, namely 2, 4-dinitrotoluene, for reaction, collecting filtrate, and adding tetrabutylammonium bromide, manganese dioxide and hydrogen peroxide for reaction to obtain white solid; allowing N, N-dimethyl formamide, sodium fluoride, white solid and tetrabutylammonium bromide for reaction to obtain 2, 4-difluorobenzoic acid. The synthetic method is simple tooperate and high in target product yield.

Preparing method of 2,4-difluorobenzoic acid

The invention discloses a preparing method of 2,4-difluorobenzoic acid. According to the method, 2,4-dinitritoluene serves as a raw material, and a drug intermediate 2,4-difluorobenzoic acid is prepared through oxidization and fluorination, wherein potassium permanganate serves as an oxidizing agent, and potassium fluoride serves as a fluorinating agent. The synthesis method of the 2,4-difluorobenzoic acid is simple in technology, environmentally friendly, high in yield, and low in cost. According to the method, the total yield is 66%, and is obviously higher than that of other methods in theprior art.

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd-Co(CO)4] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates). (Figure presented.).

New method for non-metal catalytic oxidation synthesis of substituted benzoic acid compound

The invention discloses a method for synthesis of a substituted benzoic acid compound, a Wittig reagent and hydrogen peroxide as raw materials are reacted by heating in an organic solvent at reaction temperature of room temperature or 50 DEG C, the reaction formula is as shown in the specification, in the formula, Ar is an aromatic ring substituent, X is an unsaturated ester substituent or an aromatic ring substituent. The method has the following beneficial effects: (1) the method has the advantages of simple operation, wide substrate application range, high yield, friendliness to the environment; (2) the Wittig reagent is simple in preparation, the raw materials are cheap, the Wittig reagent which is not participated in the reaction can also be recycled by recrystallization; (3) the reaction conditions of the Wittig reagent and the hydrogen peroxide are mild, and the post treatment is simple, the method is green and environmentally-friendly and is suitable for industrial enlargement; and (4) by-product triphenylphosphine oxide is also recyclable, is an important chemical raw material and can be applied as organic synthesis intermediates, pharmaceutical intermediates, catalysts and extractants.

Palladium-Catalyzed Ligand-Controlled Selective Synthesis of Aldehydes and Acids from Aryl Halides and Formic Acid

Selective synthesis is in the core of modern organic chemistry. In this communication, a novel ligand-dependent palladium-catalyzed carbonylation procedure for the divergent synthesis of aldehydes and carboxylic acids from easily available aryl halides was established. Under the same reaction conditions, the reaction pathway could be controlled by the ligands applied to give formylated and carboxylated products selectively. Sterically hindered monodentate ligands facilitated the reductive carbonylation and provided aldehydes, whereas bidentate ligands preferred the carboxylation reaction and produced carboxylic acids. A wide range of functional groups were tolerated, and the products were, in general, obtained in moderate to excellent yields.

An outstanding catalyst for the oxygen-mediated oxidation of arylcarbinols, arylmethylene and arylacetylene compounds

A convenient and sustainable protocol for the aerobic oxidation of benzyl alcohols to carbonyl compounds, based on the use of 1,2,4-triazole-type ligands and nickel(ii) bromide, is described. This combination leads to the formation of an exceedingly active, enzyme-like system that allows for other oxidative processes, such as benzylic C-H oxidation and oxygen-mediated cleavage of C-C triple bond, a pioneering procedure for transformation of alkynes into carboxylic acids.

An efficient one pot method for synthesis of carboxylic acids from nitriles using recyclable ionic liquid [bmim]HSO4 Dedicated to my mentor Professor (Mrs.) Krishna Misra on her 76th birthday

Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.