4-Fluoro-2-methoxy-5-methylbenzoic acid

Base Information

• Chemical Name: 4-Fluoro-2-methoxy-5-methylbenzoic acid
• CAS No.: 314298-17-4
• Molecular Formula: C₉H₉FO₃
• Molecular Weight: 184.167
• DSSTox Substance ID: DTXSID201278995
• Mol file: 314298-17-4.mol

Synonyms:4-fluoro-2-methoxy-5-methylbenzoic acid;314298-17-4;Benzoic acid, 4-fluoro-2-methoxy-5-methyl-;4-fluoro-2-methoxy-5-methyl-benzoic acid;SCHEMBL5466375;GBWKCZYUHSAALB-UHFFFAOYSA-N;DTXSID201278995;4-fluoro-2-methoxy-5-methylbenzoicacid

Chemical Property of 4-Fluoro-2-methoxy-5-methylbenzoic acid

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 184.05357231
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1F)OC)C(=O)O

Technology Process of 4-Fluoro-2-methoxy-5-methylbenzoic acid

There total 6 articles about 4-Fluoro-2-methoxy-5-methylbenzoic acid 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: 96.0%

4-fluoro-2-methoxy-5-methyl-benzonitrile (314298-16-3) → 4-fluoro-2-methoxy-5-methyl-benzoic acid (314298-17-4)

Guidance literature:

With hydrogenchloride; In sodium hydroxide;

Reference yield: 12.0%

4-fluoro-2-methoxy-benzoic acid (395-82-4) → 4-fluoro-2-methoxy-6-methylbenzoic acid (960531-75-3) + 4-fluoro-2-methoxy-5-methyl-benzoic acid (314298-17-4)

Guidance literature:

4-fluoro-2-methoxy-benzoic acid; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -80 ℃; for 0.5h;

With methyl iodide; In tetrahydrofuran; cyclohexane; at -80 - 20 ℃;

With hydrogenchloride; water; In ethyl acetate;

Reference yield:

5-methoxy-2-methyl-4-nitroaniline (106579-00-4) → 4-fluoro-2-methoxy-5-methyl-benzoic acid (314298-17-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / pyridine; HF-pyridine; sodium nitrite / -70 - 60 °C

2: 99 percent / H₂ / Pd-C / ethanol / 760 Torr

3: 47 percent / aq. HBr; sodium nitrite; CuBr / 2.5 h / 110 °C

4: 86 percent / dimethylformamide / 20 h / 160 °C

5: 96 percent Turnov_. / aq. NaOH / 19 h / 90 °C

With pyridine; sodium hydroxide; hydrogen bromide; hydrogen; pyridine hydrogenfluoride; copper(I) bromide; sodium nitrite; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.07.062

upstream raw materials:

4-fluoro-2-methoxy-5-methyl-benzonitrile

4-fluoro-2-methoxy-benzoic acid

5-methoxy-2-methyl-4-nitroaniline

1-bromo-4-fluoro-2-methoxy-5-methyl-benzene

Downstream raw materials:

N-(4-bromo-2-fluorobenzyl)-4-fluoro-2-methoxy-5-methyl-benzamide

[2-(4-bromo-2-fluorobenzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester

[2-(4-bromo-2-fluorobenzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester

N-(4-bromo-2-fluorobenzyl)-4-fluoro-2-hydroxy-5-methyl-benzamide