2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester

Base Information

• Chemical Name: 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester
• CAS No.: 866954-86-1
• Molecular Formula: C₁₅H₁₅F₃O₅
• Molecular Weight: 332.276
• UNII: PUB2X8C9J5
• Mol file: 866954-86-1.mol

Synonyms:866954-86-1;2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester;Ethyl (Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate;ethyl (Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)prop-2-enoate;2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylicAcidEthylEster;ZIMIAPVHHUISPY-CLFYSBASSA-N;starbld0000751;PUB2X8C9J5;SCHEMBL9142948;(Z)-ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate;Ethyl (2Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate;Ethyl (alphaZ)-alpha-(ethoxymethylene)-2,4,5-trifluoro-3-methoxy-beta-oxobenzenepropanoate;Benzenepropanoic acid, alpha-(ethoxymethylene)-2,4,5-trifluoro-3-methoxy-beta-oxo-, ethyl ester, (alphaZ)-

Chemical Property of 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 332.08715806
• Heavy Atom Count: 23
• Complexity: 454

Purity/Quality:

99% ^*data from raw suppliers

2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC=C(C(=O)C1=CC(=C(C(=C1F)OC)F)F)C(=O)OCC
• Isomeric SMILES: CCO/C=C(/C(=O)C1=CC(=C(C(=C1F)OC)F)F)\C(=O)OCC
• Uses: 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester is used in the preparation Gatifloxacin (G250000) and key intermediates for the synthesis third-generation fluoroquinolone antibiotics.

Technology Process of 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic Acid Ethyl Ester

There total 4 articles about 2-(2,4,5-Trifluoro-3-methoxybenzoyl)-3-ethoxyacrylic 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: 100.0%

orthoformic acid triethyl ester (122-51-0) + ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate (112811-68-4) → ethyl (2Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (866954-86-1)

Guidance literature:

With acetic anhydride; at 120 - 150 ℃; for 1.5 - 3h; Product distribution / selectivity;

Reference yield:

3-methoxy-2,4,5-trifluorobenzoic acid (112811-65-1) → ethyl (2Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (866954-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (COCl)2; DMF / CH₂Cl₂

2.1: MgCl₂; Et₃N / acetonitrile / 20 - 25 °C

2.2: Et₃N / acetonitrile / 18 h / 20 °C

3.1: Ac₂O / 4 h / Heating

With oxalyl dichloride; acetic anhydride; triethylamine; N,N-dimethyl-formamide; magnesium chloride; In dichloromethane; acetonitrile;

DOI:10.1021/jm0497895

Reference yield:

2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → ethyl (2Z)-3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (866954-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MgCl₂; Et₃N / acetonitrile / 20 - 25 °C

1.2: Et₃N / acetonitrile / 18 h / 20 °C

2.1: Ac₂O / 4 h / Heating

With acetic anhydride; triethylamine; magnesium chloride; In acetonitrile;

DOI:10.1021/jm0497895

upstream raw materials:

orthoformic acid triethyl ester

ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate

3-methoxy-2,4,5-trifluorobenzoic acid

2,4,5-trifluoro-3-methoxybenzoyl chloride

Refernces

• 1、 Baker, William R.,Cai, Shaopei,Dimitroff, Martin,Fang, Liming,Huh, Kay K.,Ryckman, David R.,Shang, Xiao,Shawar, Ribhi M.,Therrien, Joseph H.. "A prodrug approach toward the development of water soluble fluoroquinolones and structure-activity relationships of quinoline-3-carboxylic acids". . p. 4693 - 4709. Retrieved 2007/10/03.