5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde

Base Information

• Chemical Name: 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde
• CAS No.: 570424-28-1
• Molecular Formula: C₂₂H₂₂BClN₂O₃
• Molecular Weight: 408.692
• Mol file: 570424-28-1.mol

Synonyms:5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde

Chemical Property of 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde

There total 5 articles about 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde 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: 55.0%

5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde (60367-52-4) + 2-(4-bromomethyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane (143805-78-1) → 5-chloro-1-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzyl]-2-phenyl-1H-imidazole-4-carbaldehyde + 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde (570424-28-1)

Guidance literature:

With potassium carbonate; In 1,2-dimethoxyethane; for 6h; Heating;

DOI:10.1021/jo034372c

Reference yield:

5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde (60367-52-4) + 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane (380481-66-3) → 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde (570424-28-1)

Guidance literature:

5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane; With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); In cyclohexane; at 79 ℃;

5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde; With tetrabutylammomium bromide; potassium carbonate; In 1,2-dimethoxyethane; at 75 - 80 ℃; for 4h;

DOI:10.1021/jo034372c

Reference yield:

para-bromotoluene (106-38-7) → 5-chloro-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-2-phenyl-3H-imidazole-4-carbaldehyde (570424-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / heptane; tetrahydrofuran / 0.75 h / -78 °C

1.2: B(Oi-Pr)3 / tetrahydrofuran; heptane / 2 h / -78 - -10 °C

1.3: 50 percent / acetic acid / tetrahydrofuran; heptane / -10 - 20 °C

2.1: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione; AIBN / cyclohexane / 79 °C

2.2: 13.5 kg / Bu₄NBr; K₂CO₃ / 1,2-dimethoxy-ethane / 4 h / 75 - 80 °C

With n-butyllithium; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; n-heptane; cyclohexane;

DOI:10.1021/jo034372c

upstream raw materials:

5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde

2-(4-bromomethyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane

5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane

para-bromotoluene

Downstream raw materials:

3-[4-(4-chloro-5-formyl-2-phenyl-imidazol-1-ylmethyl)phenyl]-5-isobutylthiophene-2-(3-ethyl) sulfonylurea