20397-58-4

Upstream product

• 136-60-7 benzoic acid, butyl ester 
• 2356-16-3 ethyl(diethylphosphono)(fluoro)acetate 
• 14064-10-9 diethyl 2-chloromalonate 
• 100-52-7 benzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 565-53-7 ethyl dibromofluoroacetate 
• 1479-22-7 ethyl 2-fluoro-3-oxo-3-phenylpropionate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1522-41-4 ethyl-2-fluoroacetoacetate 
• 98-88-4 benzoyl chloride 
• 171916-53-3 triethyl 2-fluoro-3-oxo-2-phosphono-3-phenylpropanoate 
• 133512-75-1 (2R,3S)-2,3-Dibromo-2-fluoro-3-phenyl-propionic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 7582-61-8 diethyl 2-oxo-3-fluorobutan-1,4-dioate sodium salt 

Downstream Products

• 147410-59-1 (E)-2-fluoro-3-phenylprop-2-en-1-ol 
• 457-45-4 (±)-2-fluoro-3-phenylpropanoic acid 
• 400092-11-7 (E)-2-fluoro-3-phenylprop-2-enyl acetate 

Relevant academic research and scientific papers

Acylation of Fluorocarbethoxy-Substituted Ylids: A Simple and General Route to α-Fluoro β-Keto Esters

(Fluorocarbethoxymethylene)tri-n-butylphosphorane (3) reacts with acid chlorides and anhydrides to form the corresponding carbon acylated phosphonium salt 4, and hydrolysis of 4 under mild basic conditions provides RCOCFHCOOEt (8) in moderate yields.The reaction is applicable to primary, secondary, tertiary, cyclic, aromatic, and ester-substituted acid chlorides.Acylation with ethyl chloroformate and ethyl chlorothioformate leads to the diesters CFH(COOEt)2 and EtSCOCFHCOOEt.Extension of this reaction sequence to perfluorinated and partially fluorinated acid chlorides did not proceed cleanly to give the expected phosphonium salts.However, the anion derived from (EtO)2P(O)CFHC(O)OEt reacts with RFCOCl to form the corresponding C-acylated phosphonates 10, and hydrolysis of 10 gives RFCOCFHCOOEt.

Preparation of fluorinated alkenes in ionic liquids

The utility of ionic liquids (8-ethyl-1,8-diazabicyclo[5,4,0]-7-undecene trifluoromethanesulfonate and 8-methyl-1,8-diazabicyclo[5,4,0]-7-undecene trifluoromethanesulfonate) as a safe recyclable reaction medium for the synthesis of α-fluoro-α,β-unsaturate

ONE-POT SYNTHESIS OF α-FLUORO-α,β-UNSATURATED ESTERS FROM CHLOROMALONIC ESTER AND CARBONYL COMPOUNDS USING "SPRAY-DRIED" POTASSIUM FLUORIDE

α-Fluoro-α,β-unsaturated esters were prepared by one-pot reaction between aldehydes or ketones and diethyl chloromalonate in the "spray-dried" potassium fluoride-sulfolane system.

A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation

The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.

Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles

Treatment of β-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 °C for 0.25 to 24 h gave γ-products in a highly regioselective manner. Thus obtained γ-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields.

P[N(i-Bu)CH2CH2]3N: Nonionic Lewis base for promoting the room-temperature synthesis of α,β-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth - Emmons phosphonates

The bicyclic triaminophosphine P(RNCH2CH2) 3N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of α,β-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and cyclic aldehydes and ketones, using a range of Wadsworth-Emmons (WE) phosphonates. Among the analogues of 1c [R = Me (1a), i-Pr (1b), Bn (1d)], 1a and 1b performed well, although longer reaction times were involved, and 1d led to poorer yields than 1c. Functionalities such as cyano, chloro, bromo, methoxy, amino, ester, and nitro were well tolerated. We were able to isolate and characterize (by X-ray means; see above) the reactive WE intermediate species formed from 2b and 1c.

Microwave-assisted one-pot synthesis of α-fluoro-α,β- unsaturated esters under solvent-free conditions

A microwave-assisted approach for the synthesis of α-fluoro-α, β-unsaturated esters from ethyl bromofluoroacetate, aldehydes, and triphenylphosphine in the presence of Zn-Cu under solvent-free conditions was achieved. The reaction was accomplished within

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

Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction

The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th

The one-pot Wittig reaction: A facile synthesis of α,β- unsaturated esters and nitriles by using nanocrystalline magnesium oxide

Nanocrystalline magnesium oxide was found to be an effective heterogeneous, solid base catalyst for the one-pot Wittig reaction to afford α,β-unsaturated esters and nitriles in excellent yields with high E-stereoselectivity in the presence of triphenylphosphine under mild conditions.