2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic acid

Base Information

• Chemical Name: 2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic acid
• CAS No.: 145066-95-1
• Molecular Formula: C16H11 Br O3
• Molecular Weight: 331.166
• DSSTox Substance ID: DTXSID30877929
• Nikkaji Number: J527.076F
• Wikidata: Q82859832
• Mol file: 145066-95-1.mol

Synonyms:145066-95-1;SCHEMBL7312942;DTXSID30877929;VKULSLZPQDWTKV-UHFFFAOYSA-N;GR-127810X;2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid;Benzoic acid, 2-(3-bromo-5-methylbenzofuran-2-yl

Chemical Property of 2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic acid

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 329.98916
• Heavy Atom Count: 20
• Complexity: 373

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)OC(=C2Br)C3=CC=CC=C3C(=O)O

Technology Process of 2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic acid

There total 4 articles about 2-(3-Bromo-5-methyl-2-benzofuranyl)benzoic 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: 92.0%

methyl 2-(3-bromo-5-methyl-2-benzofuranyl)benzoate (143381-74-2) → 2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (145066-95-1)

Guidance literature:

With sodium hydroxide; In methanol; for 3h; Heating;

DOI:10.1021/jm00045a016

Reference yield:

5-methylbenzofuran (18441-43-5) → 2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (145066-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na₂CO₃

2: 100 percent / Br₂ / CCl₄ / 0.67 h / 0 - 5 °C

3: 92 percent / aq. NaOH / methanol / 3 h / Heating

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; bromine; sodium carbonate; In methanol; tetrachloromethane;

DOI:10.1021/jm00045a016

Reference yield:

2-bromobenzoic acid methyl ester (610-94-6) → 2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (145066-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na₂CO₃

2: 100 percent / Br₂ / CCl₄ / 0.67 h / 0 - 5 °C

3: 92 percent / aq. NaOH / methanol / 3 h / Heating

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; bromine; sodium carbonate; In methanol; tetrachloromethane;

DOI:10.1021/jm00045a016

upstream raw materials:

methyl 2-(3-bromo-5-methyl-2-benzofuranyl)benzoate

5-methylbenzofuran

2-bromobenzoic acid methyl ester

methyl 2-(5-methyl-2-benzofuranyl)benzoate

Downstream raw materials:

1,1-dimethylethyl <2-(3-bromo-5-methyl-2-benzofuranyl)phenyl>carbamate

1,1-dimethylethyl 2-(3-bromo-5-methyl-2-benzofuranyl)benzoate

1,1-dimethylethyl 2-<3-bromo-5-(bromomethyl)-2-benzofuranyl>benzoate

1,1-dimethylethyl <2-(3-bromo-5-(bromomethyl)-2-benzofuranyl)phenyl>carbamate