2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine

Base Information

• Chemical Name: 2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine
• CAS No.: 276670-27-0
• Molecular Formula: C₁₇H₁₉BBrNO₂
• Molecular Weight: 360.058
• Mol file: 276670-27-0.mol

Synonyms:2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine

Chemical Property of 2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine

There total 1 articles about 2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine 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: 58.0%

2-Bromo-5-(trimethylstannyl)pyridine (225932-26-3) + 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73852-88-7) → 2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine (276670-27-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 48h; Heating;

DOI:10.1055/s-2000-6344

Reference yield: 63.0%

2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine (276670-27-0) + 4'-Bromo-3-hexyloxymethyl-5-iodobiphenyl (276670-19-0) → 2-Bromo-5-(4''-bromo-5'-hexyloxymethyl-[1,1';3',1'']-terphenyl-4-yl)pyridine (276670-26-9)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 48h; Heating;

DOI:10.1055/s-2000-6344

Reference yield:

2-Bromo-5-[4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)phenyl]pyridine (276670-27-0) → 5,5'-bis{4''-bromo-5'-(hexyloxymethyl)-[1,1';3',1'']terphenyl-4-yl}-[2,2']bipyridinyl

Guidance literature:

Multi-step reaction with 2 steps

1.1: (PPh₃)4Pd; Na₂CO₃ / toluene; H₂O / 48 h / Heating

2.1: BuLi / diethyl ether; hexane / 2 h / -78 °C

2.2: Me₃SnCl / diethyl ether; hexane / -78 - 20 °C

2.3: 40.2 percent / (PPh₃)4Pd / toluene / 24 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium carbonate; In diethyl ether; hexane; water; toluene; 1.1: Arylation / 2.1: Dehalogenation / 2.2: Metallation / 2.3: Arylation;

DOI:10.1002/1099-0690(200010)2000:20<3475::aid-ejoc3475>3.0.co;2-z

upstream raw materials:

2-Bromo-5-(trimethylstannyl)pyridine

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2-Bromo-5-(4''-bromo-5'-hexyloxymethyl-[1,1';3',1'']-terphenyl-4-yl)pyridine