331-25-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorophenylacetic acid is used as a building block for the synthesis of pentaamine and bis-heterocyclic libraries, which are essential in the development of new drugs and therapeutic agents. Its role in creating these libraries is vital for expanding the range of available medications and treatments for various medical conditions.
Used in Chemical Synthesis:
3-Fluorophenylacetic acid is also utilized as a medicine intermediate, playing a significant role in the production of various pharmaceutical compounds. Its presence in the synthesis process allows for the creation of a wide array of medications, contributing to the advancement of medical research and the development of novel treatments.

InChI:InChI=1/C8H7FO2/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Upstream product

• 501-00-8 3-fluorophenylacetonitrile 
• 6929-49-3 m-Fluoro-ω-diazoacetophenon 
• 1711-07-5 3-fluorobenzoyl chloride 
• 456-42-8 m-fluorobenzyl chloride 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 124-38-9 carbon dioxide 
• 456-88-2 3-fluorophenylalanine 
• 95041-89-7 3-(3-fluoro-phenyl)-2-oxo-propionic acid 
• 75321-89-0 2-(3-fluorophenyl)acetaldehyde 
• 163733-96-8 3,4,5-trifluoro aniline 
• 350-51-6 3-fluorostyrene 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 64-19-7 acetic acid 
• 201230-82-2 carbon monoxide 

Downstream Products

• 587-47-3 3-fluorophenylacetic acid ethyl ester 
• 52059-53-7 2-(3-fluorophenyl)ethanol 
• 143033-76-5 Acetic acid 6-(3-fluoro-phenyl)-7-oxo-7H-dibenzo[a,c]cyclohepten-5-yl ester 
• 38693-99-1 (E)-4-<2-(3-fluorophenyl)ethenyl>phenol 
• 221121-29-5 2-(3-Fluoro-phenyl)-1-imidazol-1-yl-ethanone 
• 150544-00-6 methyl (5-fluoro-2,4-dinitrophenyl)acetate 
• 64123-77-9 methyl (3-fluorophenyl)acetate 
• 411235-93-3 4-(4-acetoxyphenyl)-3-(3-fluorophenyl)-7-methoxychromen-2-one 
• 1026356-34-2 4-[2-(3-fluoro-phenyl)-acetylamino]-piperidine-1-carboxylic acid tert-butyl ester 
• 745061-52-3 N-(5,6-dimethoxy-indan-2-yl)-2-(3-fluoro-phenyl)-N-propyl-acetamide 
• 304649-65-8 4-fluoro-2-(methoxycarbonylmethyl)benzenesulfonamide 

Relevant academic research and scientific papers

Visible-Light-Enabled Carboxylation of Benzyl Alcohol Derivatives with CO2 Using a Palladium/Iridium Dual Catalyst

A highly efficient carboxylation of benzyl alcohol derivatives with CO2 using a palladium/iridium dual catalyst under visible-light irradiation was developed. A wide range of benzyl alcohol derivatives could be employed to provide benzylic carboxylic acids in moderate to high yields. Mechanistic studies indicated that the oxidative addition of benzyl alcohol derivatives was possibly the rate-determining-step. It was also found that a switchable site-selective carboxylation between benzylic C?O and aryl C?Cl moieties could be achieved simply by changing the palladium catalyst.

Efficient Synthesis of Phenylacetate and 2-Phenylethanol by Modular Cascade Biocatalysis

The green and sustainable synthesis of chemicals from renewable feedstocks by a biotransformation approach has gained increasing attention in recent years. In this work, we developed enzymatic cascades to efficiently convert l-phenylalanine into 2-phenylethanol (2-PE) and phenylacetic acid (PAA), l-tyrosine into tyrosol (p-hydroxyphenylethanol, p-HPE) and p-hydroxyphenylacetic acid (p-HPAA). The enzymatic cascade was cast into an aromatic aldehyde formation module, followed by an aldehyde reduction module, or aldehyde oxidation module, to achieve one-pot biotransformation by using recombinant Escherichia coli. Biotransformation of 50 mM l-Phe produced 6.76 g/L PAA with more than 99 % conversion and 5.95 g/L of 2-PE with 97 % conversion. The bioconversion efficiencies of p-HPAA and p-HPE from l-Tyr reached to 88 and 94 %, respectively. In addition, m-fluoro-phenylalanine was further employed as an unnatural aromatic amino acid substrate to obtain m-fluoro-phenylacetic acid; '96 % conversion was achieved. Our results thus demonstrated high-yielding and potential industrial synthesis of above aromatic compounds by one-pot cascade biocatalysis.

An improved method for the synthesis of phenylacetic acid derivatives via carbonylation

2,4-Dichlorophenylacetic acid is synthesized in high yield via the carbonylation of 2,4-dichlorobenzyl chloride, and various experimental conditions are evaluated. Xylene, bistriphenylphosphine palladium dichloride, tetraethylammonium chloride and sodium hydroxide in solution are added to the reaction system and held at 80 °C under a CO atmosphere. 2,4-Dichlorophenylacetic acid is obtained in a maximum yield of 95percent, and a mechanism for 2,4-dichlorobenzyl chloride carbonylation is proposed. The reaction system provides a mild, effective and novel means by which to prepare phenylacetic acid derivatives from their corresponding benzyl chloride derivatives.

Preparation method of fluorophenylacetic acid

The invention relates to the field of chemical synthesis, and particularly relates to a preparation method of fluorophenylacetic acid. The invention provides a preparation method of fluorophenylacetic acid. The preparation method comprises the following steps: diazotization addition reaction: enabling a compound of the formula II to react in a system containing vinylidene chloride, acid, a diazonino reagent, a phase transfer catalyst and a copper catalyst to produce a compound of the formula III; and hydrolysis reaction: hydrolyzing the compound of the formula III to produce a compound of the formula I under the existence condition of acid. The preparation method is simply and easily available in raw materials, simple and convenient to operate, low in raw material cost, mild in reaction conditions, and low in danger, free from the use of high-price noble metal catalyst and complicated industrial operation means, and the quality of the product is stable, and therefore, the preparation method is suitable for industrial large-scale production.

Regio- and Stereoselective Oxidation of Styrene Derivatives to Arylalkanoic Acids via One-Pot Cascade Biotransformations

Green and selective oxidation methods are highly desired in chemical synthesis and manufacturing. In this work, we have developed a biocatalytic method for the regio- and stereoselective oxidation of styrene derivatives into arylacetic and (S)-2-arylpropionic acids via a one-pot epoxidation–isomerization–oxidation sequence. This was done via the engineering of Escherichia coli (StyABC-EcALDH) coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI) and aldehyde dehydrogenase (EcALDH) as an active and easily available whole-cell catalyst. Regioselective oxidation of styrene and 11 substituted styrenes using the E. coli cells was performed in a one-pot set-up, producing 12 phenylacetic acids in both high conversion and high yield. Engineering of E. coli (StyABC-ADH9v1) coexpressing SMO, SOI and ADH9v1 (a mutated alcohol dehydrogenase) led to biocatalysts capable of regio- and stereoselective oxidation of α-methylstyrene derivatives to the corresponding chiral acids. One-pot asymmetric synthesis of 4 (S)-2-arylpropionic acids was achieved in good conversion and excellent ee with the E. coli cells. This is a new type of asymmetric alkene oxidation to give chiral acids with no chemical counterpart thus far. The cascade bio-oxidation operates under mild conditions, uses molecular oxygen, exhibits very high regio- and enantioselectivity, and gives high conversion, thus providing a green and efficient method for the synthesis of arylacetic acids and (S)-2-arylpropionic acids directly from easily available styrenes. (Figure presented.).

Palladium-Catalyzed Carboxylation of Benzyl Chlorides with Atmospheric Carbon Dioxide in Combination with Manganese/Magnesium Chloride

An efficient direct carboxylation of a series of benzyl chlorides with CO2 catalyzed by Pd(OAc)2/dicyclohexyl (2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) was developed to afford the corresponding phenylacetic acids in combination with Mn powder as a reducing reagent and MgCl2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO2. The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl2 is able to stabilize the (SPhos)2PdII(Bn)(Cl)(η1-CO2)(MgCl2) adduct and thus facilitates CO2 insertion into the PdII-C bond, which is supported by a DFT study. Specific effect: MgCl2 facilitates the direct insertion of CO2 into the PdII-C bond by stabilizing the PdII-CO2 adduct. With MgCl2 as an indispensable additive, the Pd-catalyzed carboxylation of various benzyl chlorides proceeded smoothly under 1 atm CO2, and the application of Mn powder instead of a sensitive reducing reagent makes this protocol an operationally simple access to phenylacetic acids.

Palladium-catalyzed silver-mediated α-arylation of acetic acid: A new approach for the α-arylation of carbonyl compounds

A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides was developed. This protocol provided a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Palladium served on a silver platter: A new approach for the α-arylation of acetic acid through Pd-catalyzed silver-mediated direct C-H arylation of acetic acid with aryl iodides is presented. This protocol provides a straightforward method for the synthesis of a diverse set of α-phenylacetic acids. Deuteration experiments are performed to help elucidate the reaction mechanism.

An efficiently cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives

A highly efficient cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives under one atmosphere pressure is reported. This methodology represents a useful extension of benzimidazole used as ligand in metal catalysis, and the catalytic mechanism has been proved by computer simulation. Notably, this new cobalt precatalyst, which promotes the carbonylation reaction dramatically and has already been used for scale-up experiment of phenylacetic acid derivatives.

Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents

A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.

Photolysis of the 1-naphthylmethyl ester of substituted phenylacetic acids: intramolecular charge transfer and rates of decarboxylation of arylacyl radicals

The photolysis of esters 6 and 8 in methanol leads to products resulting from both naphthylmethyl cations and radicals.The product distribution is nearly independent of X for the esters 6 except when X equals methoxy.A mechanism involving initial homolytic cleavage of the carbon-oxygen bond in the excited singlet state of the ester is proposed.Competition between electron transfer in the radical pair to form the ion pair and decarboxylation of the arylacyloxy radical allows calculations of the rates of this decarboxylation process.The ρ values versus ? is close to zero.When X equals methoxy, intramolecular electron transfer occurs with the naphthalene ring serving as the acceptor and the methoxyaromatic as the donor.This exciplex fragments to carbon dioxide and 1-(1-naphthyl)-2-arylethane. Key words: acyloxy radical, decarboxylation, photolysis of benzylic esters.