Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate

Base Information

• Chemical Name: Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate
• CAS No.: 194804-99-4
• Molecular Formula: C12H12 Br F O4
• Molecular Weight: 319.127
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID60582877
• Wikidata: Q82474378
• Mol file: 194804-99-4.mol

Synonyms:194804-99-4;ETHYL 3-(4-BROMO-2-FLUORO-3-METHOXYPHENYL)-3-OXOPROPANOATE;3-(4-BROMO-2-FLUORO-3-METHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;C12H12BrFO4;PCDAFJXGOUJVGR-UHFFFAOYSA-N;SCHEMBL589507;DTXSID60582877;AB1421;MFCD06658439;3-(4-Bromo-2-fluoro-3-methoxyphenyl)-3-oxo-propionic acid ethyl ester;AKOS024260398;SB34829;CS-0340922;A813752;ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropionate;ETHYL3-(4-BROMO-2-FLUORO-3-METHOXYPHENYL)-3-OXOPROPANOATE;3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoic acid ethyl ester

Chemical Property of Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate

Chemical Property:

• Melting Point: 52-53 °C
• Boiling Point: 363.9±42.0 °C(Predicted)
• PKA: 10.17±0.50(Predicted)
• PSA: 52.60000
• Density: 1.461±0.06 g/cm3(Predicted)
• LogP: 2.73270
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 317.99030
• Heavy Atom Count: 18
• Complexity: 311

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=C(C(=C(C=C1)Br)OC)F

Technology Process of Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate

There total 6 articles about Ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropanoate 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:

4-bromo-2-fluoro-3-methoxybenzoic acid chloride + hydrogen ethyl malonate (1071-46-1) → ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropionate (194804-99-4)

Guidance literature:

hydrogen ethyl malonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

4-bromo-2-fluoro-3-methoxybenzoic acid chloride; In tetrahydrofuran; hexane; dichloromethane; at -78 - 10 ℃;

DOI:10.1021/jm060844e

Reference yield:

2-fluoro-6-nitrophenol (1526-17-6,34470-85-4) → ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropionate (194804-99-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / dimethylformamide / 6 h / 80 °C

2.1: H₂ / Pd/C / methanol / 27 h / 20 °C

3.1: aq. HBr; NaNO₂ / 0 - 5 °C

3.2: CuBr; aq. HBr / 60 °C

4.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C

4.2: tetrahydrofuran; hexane / -78 - 20 °C

5.1: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

6.1: n-BuLi / hexane; tetrahydrofuran / -78 °C

6.2: 4.70 g / hexane; tetrahydrofuran; CH₂Cl₂ / -78 - 10 °C

With n-butyllithium; oxalyl dichloride; hydrogen bromide; hydrogen; potassium carbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 3.2: Sandmeyer reaction;

DOI:10.1021/jm060844e

Reference yield:

1-fluoro-2-methoxy-3-nitrobenzene (484-94-6) → ethyl 3-(4-bromo-2-fluoro-3-methoxyphenyl)-3-oxopropionate (194804-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd/C / methanol / 27 h / 20 °C

2.1: aq. HBr; NaNO₂ / 0 - 5 °C

2.2: CuBr; aq. HBr / 60 °C

3.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C

3.2: tetrahydrofuran; hexane / -78 - 20 °C

4.1: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / -78 °C

5.2: 4.70 g / hexane; tetrahydrofuran; CH₂Cl₂ / -78 - 10 °C

With n-butyllithium; oxalyl dichloride; hydrogen bromide; hydrogen; N,N-dimethyl-formamide; lithium diisopropyl amide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.2: Sandmeyer reaction;

DOI:10.1021/jm060844e

upstream raw materials:

hydrogen ethyl malonate

1-bromo-3-fluoro-2-methoxybenzene

4-bromo-2-fluoro-3-methoxybenzoic acid

2-fluoro-6-nitrophenol