2343-89-7

Usage

Uses

Used in Organic Synthesis:
METHYL 2-FLUOROACRYLATE is used as a crucial intermediate for the synthesis of various organic compounds. Its unique chemical properties allow it to be a versatile building block in the creation of a wide range of molecules.
Used in Pharmaceutical Industry:
METHYL 2-FLUOROACRYLATE is used as a key component in the development of new pharmaceuticals. Its incorporation into drug molecules can potentially enhance their efficacy, safety, and pharmacokinetic properties.
Used in Agrochemicals:
METHYL 2-FLUOROACRYLATE is used as a vital intermediate in the production of agrochemicals, such as pesticides and herbicides. Its application in this industry contributes to the development of more effective and environmentally friendly products for agricultural use.

Synthesis Reference(s)

Synthetic Communications, 11, p. 901, 1981 DOI: 10.1080/00397918108065745

InChI:InChI=1/C4H5FO2/c1-3(5)4(6)7-2/h1H2,2H3

Synthetic route

Methyl 2-Fluoro-3-(4-toluenesulfonyloxy)propanoate (85345-88-6) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With potassium phtalimide at -78 - 150℃; under 0.01 Torr;	97%

Methyl 3-chloro-2-fluoropropanoate (55900-27-1) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium phosphate In 1-methyl-pyrrolidin-2-one at 150℃; under 112.511 - 225.023 Torr;	95%
With dimethyl amine In diethyl ether; benzene

methanol (67-56-1) + 2-fluoroacrylic acid (430-99-9) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With thionyl chloride at 5 - 35℃; for 2h; Concentration; Reagent/catalyst;	93%

dimethyl 2-fluoro-2-chloromethylmalonate → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; under 225.023 Torr; for 4h;	92%

methanol (67-56-1) + 1-chloro-1-fluoroethane (2317-91-1) + carbon monoxide (201230-82-2) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II); triethylamine at 100℃; under 5250.53 Torr; for 8h; Reagent/catalyst; Autoclave;	91.8%
With bis(tri-t-butylphosphine)palladium(0) at 100℃; for 18h; Reagent/catalyst; Time; Autoclave;	77.4%

methanol (67-56-1) + 1-bromo-1-fluoroethylene (420-25-7) + carbon monoxide (201230-82-2) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; lithium carbonate; triethylamine at 90℃; for 6h; Reagent/catalyst; Temperature; Autoclave;	90.7%
With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); triethylamine at 100℃; under 7500.75 Torr; for 8h; Reagent/catalyst; Autoclave;	90.1%
With bis-triphenylphosphine-palladium(II) chloride; tributyl-amine; lithium carbonate at 90℃; under 7500.75 Torr; for 6h; Reagent/catalyst; Autoclave;	71.8 g

1-chloro-1-fluoro-2,2-dimethoxycyclopropane → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; methoxybenzene at 120 - 130℃; under 500 Torr; Reagent/catalyst; Temperature;	89.5%
With 2,6-di-tert-butyl-4-methyl-phenol at 145℃; under 360 Torr;	12.3 g

methyl 3-bromo-2-fluoro-2-chloropropanoate (2365-93-7) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 10H-phenothiazine; sulfuric acid; zinc In water at 82 - 86℃; for 0.333333h;	85%
With hydrogen sulfide; sodium N-nitroso-N-phenylhydroxylaminate; zinc In water at 100℃;	82%
With zinc	80%
With sulfuric acid; zinc

C13H13FO6 → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 10H-phenothiazine In sulfolane at 180℃; for 6h;	83.9%

C14H15FO6 → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 4-methoxy-phenol at 170℃; for 9h;	81.2%

C14H25FO5 → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 10H-phenothiazine at 170℃; for 15h;	81.2%

formaldehyd (50-00-0) + methyl fluoroacetate (453-18-9) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
Stage #1: methyl fluoroacetate With Dimethyl oxalate; sodium methylate In dimethyl sulfoxide at 15 - 25℃; for 1h; Inert atmosphere; Stage #2: formaldehyd With 2,6-di-tert-butyl-4-methyl-phenol In dimethyl sulfoxide at 20 - 35℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere;	79.3%
Stage #1: methyl fluoroacetate With Dimethyl oxalate; sodium methylate In methanol; pentane at 20 - 25℃; for 24.25h; Claisen Condensation; Stage #2: formaldehyd In pentane at 5 - 10℃; for 5h; Concentration; Reagent/catalyst; Temperature; Time;	58%

methyl 2R,3S-2,3-difluoro-2,3-dichloropropionate (67832-56-8, 76497-87-5, 76548-29-3) → methyl 2-fluoroprop-2-enoate (2343-89-7) + methyl Z-α,β-difluoropropenoate (1660-56-6)

Conditions	Yield
With sulfuric acid; zinc at 100℃;	A 10% B 75%

methyl α,β-dibromo-α-fluoropropionate (380-26-7) → methyl 2-fluoroprop-2-enoate (2343-89-7) + acrylic acid methyl ester (292638-85-8)

Conditions	Yield
With thiourea; zinc In diphenylether at 95℃; under 20 Torr;	A 74% B n/a

C13H15FO7S → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In sulfolane at 140℃; for 17h;	73.8%

methyl α-bromo-α-fluoropropionate → methyl 2-fluoroprop-2-enoate (2343-89-7) + methyl 2,2-difluoropropanoate (38650-84-9)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 50℃; for 48h; Solvent; Temperature; Reagent/catalyst; Cooling with ice;	A 23% B 73%

methanol (67-56-1) + 1-bromo-1-fluoroethylene (420-25-7) + carbon monoxide (201230-82-2) → 2-fluoroacrylic acid (430-99-9) + methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With dichloro[bis(2-(diphenylphosphino)phenyl)ether]palladium(ll); triethylamine at 100℃; under 7500.75 Torr; for 13h; Autoclave;	A 14.1% B 70.9%

methyl α-bromo-α-fluoropropionate → methyl 2-fluoroprop-2-enoate (2343-89-7) + 2,2-difluoropropanoic acid (373-96-6) + methyl 2,2-difluoropropanoate (38650-84-9)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 72h; Reagent/catalyst; Solvent; Temperature; Cooling with ice;	A 18% B 5% C 70%

dimethyl 2-fluoro-2-(hydroxymethyl)malonate (107843-23-2) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With sulfolane; potassium fluoride; 2,6-di-tert-butyl-4-methyl-phenol at 90 - 105℃; under 760.051 Torr; for 1.25h;	70%
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; under 225.023 Torr;	24 g

methyl (2R,3R)-2,3-difluoro-2,3-dichloropropionate (76548-29-3) → methyl 2-fluoroprop-2-enoate (2343-89-7) + methyl Z-α,β-difluoropropenoate (1660-56-6) + methyl α,β-difluoroacrylate (76474-26-5)

Conditions	Yield
With sulfuric acid; zinc at 100℃;	A 10% B 64% C 10%

2,3-Dichlor-2-fluor-propansaeuremethylester (53510-07-9) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With sulfuric acid; water; zinc at 100 - 110℃;	52%

2,3-difluoropropionic acid methyl ester (4447-55-6) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With sodium fluoride at 30℃; for 3h;	46.9%

methanol (67-56-1) + Vinylidene fluoride (75-38-7) + carbon monoxide (201230-82-2) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
Stage #1: methanol With bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine; lithium iodide In 1,4-dioxane at -78 - 30℃; for 1.5h; Autoclave; Sealed tube; Inert atmosphere; Stage #2: Vinylidene fluoride; carbon monoxide In 1,4-dioxane at 90℃; under 3000.3 Torr; for 24h; Concentration; Solvent; Temperature; Autoclave; Sealed tube;	5%

methyl 3-bromo-2-fluoropropionate (399-86-0) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With dimethyl amine In diethyl ether; benzene

cyclopenta-1,3-diene (542-92-7) → methyl 2-fluoroprop-2-enoate (2343-89-7) + (1S,2R,4S)-2-Fluoro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester + (1R,2R,4R)-2-Fluoro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Conditions	Yield
With thiourea; zinc 1.) diphenyl ether, 95 deg C, 20 Torr, 2.) room temperature; Yield given. Multistep reaction. Yields of byproduct given;

methyl α-bromo-α-fluoropropionate → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 10H-phenothiazine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70℃; for 5h; Product distribution / selectivity;

formaldehyd (50-00-0) + C6H6FO5(1-)*Na(1+) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
Stage #1: C6H6FO5(1-)*Na(1+) In dimethyl sulfoxide for 0.333333h; Molecular sieve; Stage #2: formaldehyd In dimethyl sulfoxide at 40℃; for 1.5h; Molecular sieve;	19 g

1,1-dimethoxyethylene (922-69-0) + Dichlorofluoromethane (75-43-4) → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
Stage #1: 1,1-dimethoxyethylene; Dichlorofluoromethane With tetrabutylammomium bromide; potassium hydroxide In hexane; water at 5 - 10℃; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol at 0 - 145℃; under 360 Torr;

dimethyl 2-fluoro-2-chlorosulfinyloxymethylmalonate → methyl 2-fluoroprop-2-enoate (2343-89-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; under 225.023 Torr; for 4h;

methyl 2-fluoroprop-2-enoate (2343-89-7) + 3-methoxy-1-iodobenzene (766-85-8) → (Z)-methyl 2-fluoro-3-(3-methoxyphenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

ortho-methylphenyl iodide (615-37-2) + methyl 2-fluoroprop-2-enoate (2343-89-7) → (Z)-methyl 2-fluoro-3-(2-methylphenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

methyl 2-fluoroprop-2-enoate (2343-89-7) + o-iodo-methyl-benzoic acid (610-97-9) → (Z)-methyl 2-(2-fluoro-3-methoxy-3-oxoprop-1-en-1-yl)benzoate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 2-iodonaphthalene (612-55-5) → (Z)-methyl 2-fluoro-3-(naphth-2-yl)acrylate (1075204-23-7)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

iodobenzene (591-50-4) + methyl 2-fluoroprop-2-enoate (2343-89-7) → methyl (Z)-2-fluoro-3-phenylpropenoate (370-07-0, 56695-79-5, 56695-78-4)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Reagent/catalyst; Temperature; Heck Reaction; stereospecific reaction;	99%
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Sealed tube; Inert atmosphere;

methyl 2-fluoroprop-2-enoate (2343-89-7) + 4-fluoro-1-iodobenzene (352-34-1) → (Z)-methyl 3-(4-fluorophenyl)-2-fluoroacrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 4-Iodobenzotrifluoride (455-13-0) → methyl Z-2-fluoro-3-(4-trifluoromethylphenyl)prop-2-enoate (126976-31-6)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	99%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 2-6-dimethoxybenzoic acid (1466-76-8) → (Z)-methyl 2-fluoro-3-(2,6-dimethoxyphenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction;	98%

methyl 2-fluoroprop-2-enoate (2343-89-7) + octadec-1-ene (112-88-9) → methyl (Z)-2-fluorononadec-2-enoate

Conditions	Yield
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction;	98%

propylamine (107-10-8) + methyl 2-fluoroprop-2-enoate (2343-89-7) → N-(n-propyl)-α-fluoroacrylamide (1378386-19-6)

Conditions	Yield
In methanol at 20℃; for 24h;	96.14%

methyl 2-fluoroprop-2-enoate (2343-89-7) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → methyl 1-benzyl 3-fluoropyrrolidine-3-carboxylate (1279669-60-1)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h;	95%
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere;	80%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;

methyl 2-fluoroprop-2-enoate (2343-89-7) + 1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester (163229-48-9) → C19H22FNO6

Conditions	Yield
With [Ir(dF(Me)ppy)2dtbbpy]PF6 In tetrahydrofuran at 28℃; Inert atmosphere; Glovebox; Irradiation;	93%

methyl 2-fluoroprop-2-enoate (2343-89-7) + (R)-N-(1-phenylethyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine (133407-38-2) → methyl 3-fluoro-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (1461698-11-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	92%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 2-Methoxybenzoic acid (579-75-9) → methyl (2Z)-2-fluoro-3-(2-methoxyphenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Sealed tube; diastereoselective reaction;	92%

methyl 2-fluoroprop-2-enoate (2343-89-7) + N-methylaniline (100-61-8) → 3-fluoro-1-phenylpyrrolidin-2-one

Conditions	Yield
With Quinuclidine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile for 16h; Sealed tube; Inert atmosphere; Irradiation;	92%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 3,5-difluoro-N-hydroxybenzenecarboximidoyl chloride (677728-84-6) → methyl 3-(3,5-difluorophenyl)-5-fluoro-4,5-dihydro-1,2-oxazole-5-carboxylate

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol at 40℃; for 1h;	91%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 4-iodobenzonitrile (3058-39-7) → methyl Z-3-(4-cyanophenyl)-2-fluoroprop-2-enoate (126976-32-7)

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction;	90%
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Sealed tube; Inert atmosphere;

methyl 2-fluoroprop-2-enoate (2343-89-7) + 1,4-bromoiodobenzene (589-87-7) → (Z)-methyl 3-(4-bromophenyl)-2-fluoroacrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; chemoselective reaction;	89%

methyl 2-fluoroprop-2-enoate (2343-89-7) + mesitylenecarboxylic acid (480-63-7) → (Z)-methyl 2-fluoro-3-(2,4,6-trimethylphenyl)acrylate

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction;	89%

methyl 2-fluoroprop-2-enoate (2343-89-7) → 2-fluoroacrylic acid (430-99-9)

Conditions	Yield
Stage #1: methyl 2-fluoroprop-2-enoate With sodium hydroxide In ethanol; water for 0.5h; pH=11; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water Inert atmosphere;	87%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 4-Phenyl-1-butene (768-56-9) → (Z)-methyl 2-fluoro-4-phenyl-2-butenoate (113924-47-3) + methyl (Z)-2-fluoro-5-phenylpent-2-enoate

Conditions	Yield
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In chloroform at 80℃; for 15h; Reagent/catalyst; Solvent; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction;	A n/a B 87%

methyl 2-fluoroprop-2-enoate (2343-89-7) + 1-(but-3-en-1-yl)-2-methoxybenzene (63667-83-4) → methyl (Z)-2-fluoro-5-(2-methoxyphenyl)pent-2-enoate

Conditions	Yield
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction;	87%

1-Decene (872-05-9) + methyl 2-fluoroprop-2-enoate (2343-89-7) → methyl (Z)-2-fluoroundeca-2-enoate

Conditions	Yield
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction;	87%

Upstream product

• 380-26-7 methyl α,β-dibromo-α-fluoropropionate 
• 76548-29-3 methyl (2R,3R)-2,3-difluoro-2,3-dichloropropionate 
• 67832-56-8 methyl 2R,3S-2,3-difluoro-2,3-dichloropropionate 
• 542-92-7 cyclopenta-1,3-diene 
• 67-56-1 methanol 
• 430-99-9 2-fluoroacrylic acid 
• 4447-55-6 2,3-difluoropropionic acid methyl ester 
• 2317-91-1 1-chloro-1-fluoroethane 
• 201230-82-2 carbon monoxide 
• 85345-88-6 Methyl 2-Fluoro-3-(4-toluenesulfonyloxy)propanoate 
• 2365-93-7 methyl 3-bromo-2-fluoro-2-chloropropanoate 
• 55900-27-1 methyl 2-fluoro-3-chloropropionate 
• 922-67-8 propynoic acid methyl ester 
• 4538-50-5 methyl glycidate 

Downstream Products

• 99953-33-0 methyl 3-bromo-2,2-difluoropropanoate 
• 1279669-60-1 methyl 1-benzyl-3-fluoropyrrolidine-3-carboxylate 
• 370-07-0 2-fluoro-3-phenyl acrylic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF METHYL 2-FLUOROACRYLATE

Methods for the synthesis of methyl 2-fluoroacrylate (MFA) are provided. The methods include use of various hydrofluorination agents using a variety of starting materials and reaction schemes. The methyl 2-fluoroacrylate prepared by the methods described herein can further be used to prepare patiromer calcium sorbitex.

METHOD FOR PRODUCING alpha-FLUOROACRYLIC ACID

An object of the present invention is to provide a novel method for producing an α-fluoroacrylic acid ester compound. This problem is solved by a method for producing a compound represented by formula (1), wherein R1 and R2 are identical or different, and each represents an alkyl group or the like; and R3 is an alkyl group or the like, the method comprising step A of reacting a compound represented by formula (2) with R3—OH (3) and carbon monoxide in the presence of palladium, a double bond-containing compound (α), a diphosphine compound (β), and a base, to obtain the compound represented by formula (1) above.

METHOD OF PRODUCING HALOGENATED ACRYLIC ACID ESTER

PROBLEM TO BE SOLVED: To provide a method allowing production of a halogenated acrylic acid ester in a manner that is safe and convenient and is also suitable for industrial production, without using toxic ingredients. SOLUTION: A method of producing a compound represented by formula (4) includes reacting a compound represented by formula (1) with a compound represented by formula (2) in the presence of a base. [In the formulas, each symbol is as described in the specification.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

ONE STEP SYNTHESIS FOR ALKYL 2-FLUOROACRYLATES

A process is provided that results in an alkyl haloacrylate that is produced by reaction of a dialkyl or diaryl halomalonate with an aldehyde, preferably formalin or paraformaldehyde, and a base catalyst to produce an intermediate that is not isolated and is heated to produce the alkyl haloacrylate. This synthesis can be one pot, meaning it reacts in the same vessel and/or reaction mixture and does not require isolation of the intermediate, and provides an improved yield. In particular, a process is provided that results in an alkyl 2-fluoroacrylate.

Preparation method of methyl 2-fluoroacrylate

A preparation method of methyl 2-fluoroacrylate comprises the following steps: adding a solvent into a reaction kettle, dissolving methyl acrylate into the solvent, emptying, controlling the reactiontemperature in the reaction kettle, introducing fluorine gas, raising the temperature in the reaction kettle, removing HF under an alkaline condition to obtain a methyl 2-fluoroacrylate mother solution, and standing the mother solution; raising the temperature of the 2-fluoromethyl acrylate mother solution, and then carrying out hot filtration on the 2-fluoromethyl acrylate mother solution to obtain a 2-fluoromethyl acrylate filtrate; recrystallizing the 2-fluoromethyl acrylate filtrate to obtain crude 2-fluoromethyl acrylate; and rectifying the crude 2-fluoromethyl acrylate, and collecting the obtained fraction to obtain pure 2-fluoromethyl acrylate. The method has low requirements on equipment, can effectively inhibit the activity of F2 and reduce the generation of byproducts, can improve the yield and purity of the product, and can effectively remove the reaction raw materials and the solvent to obtain the high-purity methyl 2-fluoroacrylate.

METHOD FOR PRODUCING ALPHA-FLUORO ACRYLIC ACID ESTER, AND COMPOSITION CONTAINING HIGHLY-PURE FLUOROCYCLOPROPANE DERIVATIVE, AND COMPOSITION CONTAINING HIGHLY-PURE ALPHA-FLUORO ACRYLIC ACID ESTER

The present invention provides a production method of α-fluoroacrylate ester, a composition containing a highly-pure fluorocyclopropane derivative and a composition containing highly-pure α-fluoroacrylate ester. The present invention relates to a method of producing a compound represented by the following formula (F), including subjecting a composition containing a compound represented by the following formula (A) to a purification treatment in the order of distillation and washing with an aqueous alkali solution to give a purified product containing a compound represented by the following formula (A), and subjecting the purified product to a thermal decomposition reaction, a composition containing a highly-pure compound represented by the following formula (A), and a composition containing a highly-pure compound represented by the following formula (F), wherein R may be the same or different and is a monovalent hydrocarbon group, and X is a halogen atom:

PROCESS FOR THE PREPARATION OF FLUOROACRYLIC ACID ESTERS

The present invention provides a process for the preparation of a compound of Formula VI.

Preparation method for 2-fluoroacrylate

The invention discloses a preparation method for 2-fluoroacrylate. The preparation method comprises the following steps: (1) mixing dichlorofluoromethane and vinyl ether with a structure as shown in a formula A so as to obtain a substituted cyclopropane compound with a structure as shown in a formula B; (2) mixing ROH and the substituted cyclopropane compound with the structure as shown in the formula B so as to obtain an acetal product with a structure as shown in a formula C, and subjecting the acetal product to hydrolysis so as to obtain 2-fluoroacrolein with a structure as shown in a formula D, or subjecting the substituted cyclopropane compound with the structure as shown in the formula B and water to a reaction and cracking so as to obtain 2-fluoroacrolein with the structure as shown in the formula D; (3) subjecting 2-fluoroacrolein with the structure as shown in the formula D to oxidation so as to obtain 2-fluoroacrylic acid with a structure as shown in a formula E; and (4) mixing ROH and 2-fluoroacrylic acid with the structure as shown in the formula E so as to obtain 2-fluoroacrylate with a structure as shown in a formula F.

Α - fluoroacrylic acid ester

The present invention provides a method for manufacturing alpha-fluoroacrylates at a low manufacture cost without using a raw material compound having strong toxicity. The method is to manufacture the compound represented by the formula (1), and comprises the step of contacting a compound represented by formula (2) with an alkali halide to obtain the compound represented by formula (1). In the formula, R1 represents an alkyl group, and R2 represents hydrogen and can have the alkyl group, an aryl group or a miscellaneous aryl possessing a substituent group, R3 represents the alkyl group, and the definitions of other symbols are ditto.

METHOD FOR PRODUCING 2-HALOGEN-ACRYLIC ACID ESTERS

The present invention relates to a process for preparing 2-haloacrylic esters from 2-hydroxymethyl- or 2-halomethyl- or 2-chlorosulfinyloxymethyl-2-halomalonic diesters. The invention further provides novel 2-halomethyl-2-halomalonic diesters or 2-chlorosulfinyloxymethyl-2-halomalonic diesters which can be used for preparation of the 2-haloacrylic esters.