3516-87-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (pentafluorobenzoyl)acetate is used as a key intermediate in the synthesis of various pharmaceuticals. Its high reactivity and ability to form complex molecular structures make it valuable in the development of novel drug compounds.
Used in Agrochemical Industry:
Ethyl (pentafluorobenzoyl)acetate is utilized as a building block in the production of agrochemicals. Its reactivity and versatility contribute to the creation of new compounds for agricultural applications, such as pesticides and herbicides.
Used in Fragrance Industry:
Ethyl (pentafluorobenzoyl)acetate is employed as a precursor in the synthesis of fragrance ingredients. Its unique properties allow for the development of novel scents and aroma compounds.
Used as a Solvent:
Ethyl (pentafluorobenzoyl)acetate is used as a solvent in numerous chemical reactions due to its ability to dissolve a wide range of substances. Its versatility makes it suitable for various applications in the chemical industry.
Used as a Reagent:
Ethyl (pentafluorobenzoyl)acetate serves as a reagent in chemical reactions, facilitating the formation of desired products. Its high reactivity and potential for creating complex molecular structures make it a valuable component in research and development efforts.

InChI:InChI=1/C11H7F5O3/c1-2-5(18)19-3-4(17)6-7(12)9(14)11(16)10(15)8(6)13/h2-3H2,1H3

Synthetic route

pentafluorobenzoylchloride (2251-50-5) + ethyl potassium malonate (6148-64-7) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
With triethylamine; magnesium chloride	97%
With triethylamine; magnesium chloride 1.) MeCN, 20 to 25 deg C, 2.5 h, 2.) 20 to 25 deg C, 12 h; Yield given. Multistep reaction;
In acetonitrile at -5℃; Inert atmosphere;

Pentafluorobenzoic acid (602-94-8) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 30 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -10 - 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere View Scheme

hydrogen ethyl malonate (1071-46-1) + pentafluorobenzoylchloride (2251-50-5) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexanes at -78 - -20℃; Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hehanes at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water for 1h;
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran at -10 - 20℃; for 1h; Inert atmosphere; Stage #2: pentafluorobenzoylchloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	10 g

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) → (Z)-ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)acrylate (516479-35-9)

Conditions	Yield
With acetic anhydride at 120 - 130℃; for 1.5 - 4.5h; Product distribution / selectivity; Heating / reflux;	100%
With acetic anhydride at 140℃; for 5h; Inert atmosphere;

2-Amino-4,6-dimethylpyridine (5407-87-4) + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → N-(4,6-dimethyl-pyridin-2-yl)-3-hydroxy-3-pentafluorophenyl-acrylamide

Conditions	Yield
2-hydroxypyridin In toluene for 6h; Heating;	83%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) → ethyl 2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate (114226-95-8)

Conditions	Yield
for 5h; Heating;	81%
With acetic anhydride
at 145℃; for 2.5h; Inert atmosphere;

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + acetic anhydride (108-24-7) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate

Conditions	Yield
In ethanol; cyclohexane; Petroleum ether	72%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + benzaldehyde (100-52-7) → 3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one

Conditions	Yield
With potassium fluoride In ethanol for 8h; Heating;	38%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 1-oxo-3-pentafluorophenyl-1H-pyrano<4,3-b>-6,7,8,9-tetrafluorochromone

Conditions	Yield
for 0.833333h; Heating;	37%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 3-pentafluorophenyl-2H-isoxazol-5-one (29107-99-1)

Conditions	Yield
With hydroxylamine hydrochloride In ethanol

1-amino-4-ethoxycarbonyl-7-methoxy-3-phenyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidin-8-ylium; trifluoro-acetate + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → Trifluoro-acetate(2aR,8aR)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium; + Trifluoro-acetate(2aR,8aS)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium;

Conditions	Yield
With morpholinium acetate; sodium sulfate In 2,2,2-trifluoroethanol at 70℃; for 72h;	A 325 mg B 325 mg

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 5,6,7,8-tetrafluorochromone (22697-40-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 73 percent / AcOH, conc. HCl / 6 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 69 percent / AcOH, conc. HCl / 20 h / 40 - 50 °C 4: 79 percent / 190 - 200 °C View Scheme
Multi-step reaction with 3 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 1.) conc. HCl / 1.) CH3COOH, reflux, 6 h, 2.) 200 deg C View Scheme
Multi-step reaction with 4 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 69 percent / HCl / acetic acid / 20 h / 40 - 45 °C 4: 79 percent / 190 - 200 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 3-Carboxy-5,6,7,8-tetrafluorochromone (154679-02-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 69 percent / AcOH, conc. HCl / 20 h / 40 - 50 °C View Scheme
Multi-step reaction with 3 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating 3: 69 percent / HCl / acetic acid / 20 h / 40 - 45 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 3-ethoxycarbonyl-5,6,7,8-tetrafluorochromone (154679-00-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 81 percent / 5 h / Heating 2: 62 percent / H2O / 0.33 h / Heating View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone

Conditions	Yield
Multi-step reaction with 2 steps 1: 37 percent / 0.83 h / Heating 2: 43 percent / conc. HCl / acetic acid / 20 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 37 percent / 0.83 h / Heating 2: 43 percent / CH3COOH, conc. HCl / 20 h / Heating View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C11H9F5O3

Conditions	Yield
With hydrogen; [Ru(R)-SYNPHOSBr2] In ethanol at 80℃; under 7500.75 Torr; for 3h; Conversion of starting material;	n/a

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + 3-oxetanamine (21635-88-1) + orthoformic acid triethyl ester (122-51-0) → ethyl 1-(oxetan-3-yl)-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (132918-24-2)

Conditions	Yield
With acetic anhydride; potassium carbonate In N-methyl-acetamide; hexane; chloroform; benzene

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + 3-acetylaminopyrrolidine (79286-74-1) → ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate (155035-70-4)

Conditions	Yield
With triethylamine In pyridine; chloroform

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 1-phenyl-3-(pentafluorophenyl)-5-hydroxypyrazole

Conditions	Yield
With hydrogenchloride; phenylhydrazine In methanol	1.76 g (54%)

piperidine (110-89-4) + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + 3,5-Difluoro-2,4-dihydroxybenzaldehyde (209541-27-5) → 6,8-difluoro-7-hydroxy-3-pentafluorobenzoylcoumarin

Conditions	Yield
In methanol; chloroform

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + recorcinol (108-46-3) → 7-hydroxy-4-pentafluorophenylcoumarin

Conditions	Yield
In methane sulfonic acid; water

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3)

Conditions	Yield
With acetic anhydride In N-methyl-acetamide; ethanol

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → ethyl 3-cyclopropylamino-2-(2,3,4,5,6-pentafluorobenzoyl)-acrylate

Conditions	Yield
With acetic anhydride In isopropyl alcohol; pentane

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + Phenyl N-cyclopropyliminochlorothioformate (130878-55-6) → ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (193283-44-2)

Conditions	Yield
Stage #1: ethyl 2,3,4,5,6-pentafluorobenzoylacetate With sodium hydride In toluene for 0.5h; Stage #2: Phenyl N-cyclopropyliminochlorothioformate In toluene at 50℃; for 24h; Heating / reflux;

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C15H14F5NO4

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride 2: dichloromethane / 0 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C15H14F5NO4

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride 2: dichloromethane / 0 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C17H18F5NO4 (1337541-25-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride 2: dichloromethane / 0 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C17H18F5NO4

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride 2: dichloromethane / 0 °C View Scheme

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → C16H16F5NO4

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride 2: dichloromethane / 0 °C View Scheme

Upstream product

• 602-94-8 Pentafluorobenzoic acid 
• 1071-46-1 hydrogen ethyl malonate 
• 2251-50-5 pentafluorobenzoylchloride 
• 6148-64-7 ethyl potassium malonate 

Downstream Products

• 114226-95-8 ethyl-2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate 
• 155035-70-4 ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate 
• 193283-44-2 ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 103772-14-1 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 103772-13-0 ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 1352946-32-7 C₂₅H₂₄F₂N₂O₄ 
• 1352946-31-6 C₂₄H₂₂F₂N₂O₄ 
• 1352946-30-5 C₂₄H₂₄F₂N₂O₄ 
• 1352946-29-2 C₂₃H₂₂F₂N₂O₄ 
• 1352946-28-1 C₂₃H₂₂F₂N₂O₄ 
• 1352946-27-0 C₂₄H₂₄F₂N₂O₄ 
• 1337541-27-1 C₂₄H₂₄F₂N₂O₄ 
• 1352946-26-9 C₂₂H₂₀F₂N₂O₄ 
• 1352946-25-8 C₂₂H₂₀F₂N₂O₄ 

Relevant academic research and scientific papers

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The invention discloses a preparation method of ethyl (pentafluorobenzoyl)acetate. The preparation method comprises the following steps: replacing air in a reaction bottle with nitrogen which serves as protective gas, adding potassium ethyl malonate, acetonitrile and a catalyst A into the reaction bottle, carrying out stirring for 4-6 hours, performing cooling to -5 DEG C, dropwise adding pentafluorobenzoyl chloride, performing stirring for a reaction for 8 hours, and conducting drying by distillation under reduced pressure after the reaction is finished so as to obtain light yellow liquid, namely ethyl (pentafluorobenzoyl)acetate. The method is high in conversion rate and convenient for industrial production.

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