1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene

Base Information

• Chemical Name: 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene
• CAS No.: 550348-58-8
• Molecular Formula: C₃₀H₂₂F₆O₂S₂
• Molecular Weight: 592.626
• Mol file: 550348-58-8.mol

Synonyms:1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene

Chemical Property of 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene

There total 8 articles about 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene 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: 72.0%

1-[2-methyl-5-phenyl-3-thienyl]heptafluorocyclopentene (308255-22-3) + 3-bromo-5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methylthiophene (550348-57-7) → 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene (550348-58-8)

Guidance literature:

3-bromo-5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

1-[2-methyl-5-phenyl-3-thienyl]heptafluorocyclopentene; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/ol034440h

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene (550348-58-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64 percent / Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 4.5 h / Heating

2.1: 68 percent / p-TsOH*H₂O / benzene / 7 h / Heating

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

3.2: 72 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; sodium carbonate; toluene-4-sulfonic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; water; benzene;

DOI:10.1021/ol034440h

Reference yield:

3-bromo-2-methylthiophene-5-boronic acid (154566-69-5) → 1-[5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene (550348-58-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64 percent / Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran; H₂O / 4.5 h / Heating

2.1: 68 percent / p-TsOH*H₂O / benzene / 7 h / Heating

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

3.2: 72 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; sodium carbonate; toluene-4-sulfonic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; water; benzene;

DOI:10.1021/ol034440h

upstream raw materials:

1-[2-methyl-5-phenyl-3-thienyl]heptafluorocyclopentene

3-bromo-5-(4-(1,3-dioxolan-2-yl)phenyl)-2-methylthiophene

4-bromo-benzaldehyde

3-bromo-2-methylthiophene-5-boronic acid

Downstream raw materials:

1-(2-methyl-5-phenyl-3-thienyl)-2-(2-methyl-5-(4-formylphenyl)-3-thienyl)hexafluorocyclopentene

(S)-1-[5-(4-(3-methylpent-1-enyl)phenyl)-2-methyl-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)hexafluorocyclopentene