3-Chloro-2-fluoro-4-hydroxybenzoic acid

Base Information

• Chemical Name: 3-Chloro-2-fluoro-4-hydroxybenzoic acid
• CAS No.: 860296-15-7
• Molecular Formula: C₇H₄ClFO₃
• Molecular Weight: 190.558
• DSSTox Substance ID: DTXSID201280685
• Mol file: 860296-15-7.mol

Synonyms:860296-15-7;Benzoic acid, 3-chloro-2-fluoro-4-hydroxy-;3-chloro-2-fluoro-4-hydroxybenzoic acid;DTXSID201280685;AKOS016038587

Chemical Property of 3-Chloro-2-fluoro-4-hydroxybenzoic acid

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 189.9832998
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1C(=O)O)F)Cl)O

Technology Process of 3-Chloro-2-fluoro-4-hydroxybenzoic acid

There total 2 articles about 3-Chloro-2-fluoro-4-hydroxybenzoic 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: 73.0%

2-chloro-1-fluoro-3-(methoxymethoxy)benzene (860296-13-5) + carbon dioxide (124-38-9,18923-20-1) → 3-chloro-2-fluoro-4-hydroxybenzoic acid (860296-15-7)

Guidance literature:

2-chloro-1-fluoro-3-(methoxymethoxy)benzene; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -75 ℃; for 2h;

carbon dioxide; In tetrahydrofuran; hexane;

With hydrogenchloride; In water; pH=1;

DOI:10.1002/ejoc.200400895

Reference yield:

1-fluoro-3-(methoxy-methoxy)benzene (126940-10-1) → 3-chloro-2-fluoro-4-hydroxybenzoic acid (860296-15-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sec-BuLi / tetrahydrofuran; cyclohexane / 2 h / -75 °C

1.2: 83 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; cyclohexane / 0.75 h / -75 °C

2.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 2 h / -75 °C

2.2: tetrahydrofuran; hexane

2.3: 73 percent / HCl / H₂O / pH 1

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; sec.-butyllithium; In tetrahydrofuran; hexane; cyclohexane;

DOI:10.1002/ejoc.200400895

Reference yield: 89.0%

3-chloro-2-fluoro-4-hydroxybenzoic acid (860296-15-7) → 2-fluoro-4-hydroxybenzoic acid (65145-13-3)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; at 25 ℃; for 20h;

DOI:10.1002/ejoc.200400895

upstream raw materials:

2-chloro-1-fluoro-3-(methoxymethoxy)benzene

carbon dioxide

1-fluoro-3-(methoxy-methoxy)benzene

Downstream raw materials:

2-fluoro-4-hydroxybenzoic acid