2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one

Base Information

• Chemical Name: 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one
• CAS No.: 1346672-48-7
• Molecular Formula: C₂₃H₂₄BNO₃S
• Molecular Weight: 405.325
• Mol file: 1346672-48-7.mol

Synonyms:2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one

Chemical Property of 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one

There total 5 articles about 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one 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%

2-(3-bromo-2-methylphenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one (1346672-47-6) + bis(pinacol)diborane (73183-34-3) → 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one (1346672-48-7)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; for 3h; Inert atmosphere; Reflux;

Reference yield:

3-bromomethyl-benzo[b]thiophene-2-carboxylic acid methyl ester → 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one (1346672-48-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere

2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C

2.2: pH 5

3.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere

4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux

With lithium hydroxide monohydrate; water; potassium acetate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester (3133-81-1) → 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one (1346672-48-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux

2.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere

3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C

3.2: pH 5

4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux

With N-Bromosuccinimide; lithium hydroxide monohydrate; water; potassium acetate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;

upstream raw materials:

2-(3-bromo-2-methylphenyl)-1H-benzothieno[2,3-c]pyrrol-3(2H)-one

bis(pinacol)diborane

3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester

3-((3-bromo-2-methylphenylamino)methyl)benzo[b]thiophene-2-carboxylic acid