(Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester

Base Information

• Chemical Name: (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester
• CAS No.: 110915-28-1
• Molecular Formula: C₁₂H₁₀FNO₂
• Molecular Weight: 219.215
• Mol file: 110915-28-1.mol

Synonyms:(Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester

Chemical Property of (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester

There total 5 articles about (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ethyl 2-fluoroacetate (459-72-3) + 4-cyanobenzaldehyde (105-07-7) → (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester (110915-28-1)

Guidance literature:

ethyl 2-fluoroacetate; 4-cyanobenzaldehyde; With titanium tetrachloride; In dichloromethane; at 20 ℃; for 0.666667h; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 - 30 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c3ob41592a

Reference yield: 35.0%

ethyl dibromofluoroacetate (565-53-7) + 4-cyanobenzaldehyde (105-07-7) → (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester (110915-28-1)

Guidance literature:

With diethylzinc; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.201405119

Reference yield:

ethyl dibromofluoroacetate (565-53-7) + 4-cyanobenzaldehyde (105-07-7) → (2RS,3SR)-ethyl 2-bromo-2-fluoro-3-hydroxy-3-(4-cyanophenyl)propanoate + (2SR,3SR)-ethyl 2-bromo-2-fluoro-3-hydroxy-3-(4-cyanophenyl)propanoate + (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester (110915-28-1)

Guidance literature:

ethyl dibromofluoroacetate; 4-cyanobenzaldehyde; With diethylzinc; In hexane; dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

With ammonium chloride; In hexane; dichloromethane; optical yield given as %de; stereoselective reaction;

DOI:10.1021/jo900422m

upstream raw materials:

ethyl 2-fluoroacetate

4-cyanobenzaldehyde

ethyl(diethylphosphono)(fluoro)acetate

ethyl dibromofluoroacetate

Downstream raw materials:

4-((Z)-2-Ethoxycarbonyl-2-fluoro-vinyl)-benzoic acid ethyl ester

Refernces

• 1、 Augustine, John Kallikat,Bombrun, Agnes,Venkatachaliah, Srinivasa,Jothi, Anandh. "Titanium mediated olefination of aldehydes with α-haloacetates: An exceptionally stereoselective and general approach to (Z)-α-haloacrylates". . p. 8065 - 8072. Retrieved 2013/12/04.
• 2、 Elkik, Elias,Francesch, Charlette. "Preparation et spectres de RMN, H, F et C-13 d'esters α-fluoro-cinnamiques para- et meta-substitues". . p. 423 - 428. Retrieved 2007/10/02.