330-80-3

Upstream product

• 459-72-3 ethyl 2-fluoroacetate 
• 100-39-0 benzyl bromide 
• 1795-96-6 phenylalanine ethyl ester 
• 104910-33-0 ((Z)-1-Ethoxy-3-phenyl-propenyloxy)-trimethyl-silane 
• 350-99-2 ethyl (E/Z)-2-fluoro-3-phenylprop-2-enoate 
• 607-81-8 diethyl 2-benzylmalonate 
• 1578-79-6 diethyl 2-benzyl-2-fluoromalonate 
• 156002-27-6 C₁₄H₁₃FOS 
• 117751-44-7 ethyl α-fluoro-α-nitro-β-phenylpropionate 

Downstream Products

• 457-45-4 (±)-2-fluoro-3-phenylpropanoic acid 
• 110683-88-0 2-fluoro-3-phenyl-propan-1-ol 
• 151588-82-8 (2-fluoro-2-iodoethyl)benzene 
• 151588-78-2 (2-bromo-2-fluoroethyl)benzene 
• 1616366-03-0 (2-fluoro-5-phenylpentyl)benzene 
• 151588-74-8 (2-fluoro-2-chloroethyl)benzene 
• 1616366-34-7 2-(4-fluoro-5-phenylpentyl)anisole 

Relevant academic research and scientific papers

Enantioselective Suzuki cross-couplings of unactivated 1-fluoro-1-haloalkanes: Synthesis of chiral β-, γ-, δ-, and ε-fluoroalkanes

The incorporation of fluorine atom into a stereogenic center is a highly challenging transformation with current methodologies offering access mainly to chiral α- and β-fluoroalkanes. In this article, the development of a novel general approach to constru

Diastereoselective Addition of Metal α-Fluoroenolates of Carboxylate Esters to N-tert-Butylsulfinyl Imines: Synthesis of α-Fluoro-β-amino Acids

We report a diastereoselective addition reaction of fluoroacetate and α-alkylated fluoroacetate to N-tert-butylsulfinyl imines. This method provides a concise route to α-fluoro-β-amino acids containing fluorinated quaternary stereogenic carbon centers with very good yields and high diastereoselectivities. This protocol has the benefit of using abundant and readily accessible starting materials and is operationally simple. Additionally, the stereochemical outcome of the present reaction was different from that of the previously known addition of comparable nonfluorinated, brominated, and chlorinated enolates to N-sulfinyl imines, suggesting that an open transition state (rather than a closed one) is involved in the current fluoroalkylation reaction.

Efficient synthesis of secondary alkyl fluorides via suzuki cross-coupling reaction of 1-halo-1-fluoroalkanes

Organofluorine compounds have found extensive applications in various areas of science. Consequently, the development of new efficient and selective methods for their synthesis is an important goal in organic chemistry. Here, we present the first Suzuki c

Iridium-catalyzed asymmetric hydrogenation of fluorinated olefins using N,P-ligands: A struggle with hydrogenolysis and selectivity

To broaden the substrate scope of asymmetric iridium-catalyzed hydrogenation, fluorine-functionalized olefins were synthesized and hydrogenated with iridium complexes. Preliminary results showed high levels of fluorine elimination together with low selectivity. The loss of vinylic fluorine at first seemed difficult to handle, but further studies revealed that a catalyst with an azanorbornyl scaffold in the ligand gave more promising results. With this in mind, a new ligand was developed. This gave among the best results published to date for fluorine asymmetric hydrogenation, yielding high conversion and very high ee's with very little fluorine elimination. Further increasing the selectivity, the trials also revealed that tetrasubstituted fluorine-containing olefins can be hydrogenated with high ee's, despite that this class of compounds has usually shown low reactivity in this reaction type. Copyright

Simple procedure for preparation of α-fluoro esters by fluorination of ester enol silyl ethers with perchloryl fluoride

Fluorination of ester enol silyl ethers in THF at room temperature using diluted perchloryl fluoride (FClO3) in the presence of ca. 0.5M eq. of t-BuNH2 as an additive produced the corresponding α-fluoro esters in over 80% yields.

Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for generation of magnesium enolates and its application to synthesis of α-halocarboxylic acid derivatives and α-haloaldehydes

A new method for synthesis of α-halo(Cl, F)carboxylic acid derivatives and α-haloaldehydes is described. α-Halo-α-sulfinyl carboxylic acid, esters, and α-halo-α-sulfinyl aldehydes were easily prepared from aryl 1-haloalkyl sulfoxides and alkyl chloroformate and ethyl formate, respectively, in good yields. α-Chloro-α-sulfinyl amides were synthesized from (p-tolylthio)acetic acid. Ligand exchange reaction of the sulfinyl group of these acids, esters, amides, and aldehydes with ethylmagnesium bromide gave the magnesium enolates, which were treated with water to give α-halocarboxylic acid derivatives and α-chloroaldehydes in good yields. The magnesium enolates derived from the α-chloro-α-sulfinyl acid derivatives were trapped with carbonyl compounds to afford the adducts, which were transformed to α,β-epoxy carboxylic acid derivatives. Thermal elimination of the sulfinyl group in the α-halo-α-sulfinyl acid derivatives and the α-halo-sulfinyl aldehydes gave α-halo-α,β-unsaturated carboxylic acid derivatives and α-halo-α,β-unsaturated aldehydes in high yields.

Alkylation of (Fluorocarbethoxymethylene)-tri-n-butylphosphorane: A Facile Entry to α-Fluoroalkanoates

(Fluorocarbethoxymethyl)trialkylphosphonium bromides 6, prepared from ethyl bromofluoroacetate and tertiary phosphines, react with n-butyllithium in THF to give the corresponding phosphoranes 7.Reaction of the pregenerated (fluorocarbethoxymethylene)tri-n-butylphosphorane 7a with primary alkyl iodides and activated alkyl bromides followed by in situ hydrolysis of the alkylated salts provides the fluoroalkanoates 9 in a one-pot reaction.In the case of secondary alkyl halides, no substitution was observed, the main reaction being decomposition of the phosphorane.However, the anion obtained from diisopropyl (fluorocarbethoxymethyl)phosphonate 10 b reacts with CH3CH(Ph)Br and (CH3)2CHI to afford the corresponding alkylated phosphonates in good yields.Displacement of the phosphonate moiety either by base-induced hydrolysis or by reduction was unsuccessful.

A FACILE PREPARATION OF ETHYL α-FLUOROALKANOATES

Alkylation of fluorocarboalkoxymethylene tri-n-butylphosphorane followed by hydrolysis provides the title compounds in moderate to good yields.

Chemistry of Novel Compounds with Multifunctional Carbon Structure. 5. Molecular Design of Versatile Building Blocks for Aliphatic Monofluoro Molecules by Manipulation of Multifunctional Carbon Structure

Three kinds of doubly functionalized monofluoromethylene fragments, 1-fluoro-1-nitro-1-(phenylsulfonyl)alkanes (10), 2-fluoro-2-(phenylsulfonyl)alkanoic esters (11), and 2-fluoro-2-nitroalkanoic esters (12), potentially versatile building blocks for the general synthesis of various aliphatic monofluoro molecules, were prepared from the corresponding difunctional compounds 1-3 by monoalkylation (R) and selective fluorinations.The interconversion or reductive removal of each functional group in 10-12 followed by the introduction of the second alkyl groups (R') at the fluorine-bearing carbon atom was examined.Compounds 12 proved to be useful and practical building blocks for conversions to the various monofluoroalkanes 20-26.

The First Versatile and Practical Building Blocks Equivalent to the Synthon of Monofluoromethylene Dicarbanion

New monofluorinated synthons have been prepared.The use of α-fluoro-α-nitro carboxylic esters as versatile building blocks was demonstrated by their conversion to various monofluorinated compounds via fluoromethyl anion and fluoromethylene dianion equivalents.