(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

Base Information

• Chemical Name: (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline
• CAS No.: 853214-50-3
• Molecular Formula: C₁₅H₁₅BrN₂
• Molecular Weight: 303.201
• Mol file: 853214-50-3.mol

Synonyms:(E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

Chemical Property of (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline

There total 5 articles about (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline 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%

2-bromo-5-pyridylmethyl chloride (168173-56-6) + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline (853214-50-3)

Guidance literature:

With sodium hydride; triethyl phosphite; In tetrahydrofuran; mineral oil;

DOI:10.1021/acs.inorgchem.1c01992

Reference yield: 49.0%

4-dimethylamino-benzaldehyde (100-10-7) + diethyl (6-bromo-3-pyridylmethyl)phosphonate (154321-18-3) → (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline (853214-50-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; for 12h;

DOI:10.1021/acs.inorgchem.6b00972

Reference yield:

6-bromonicotinaldehyde (149806-06-4) → (E)-4-[2-(6-bromopyridin-3-yl)vinyl]-N,N-dimethylaniline (853214-50-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium tetrahydroborate; ethanol / 20 °C / Inert atmosphere

2: thionyl chloride / 1 h / -60 - 20 °C

3: 4 h / Reflux

4: sodium hydride / tetrahydrofuran; mineral oil / 12 h

With sodium tetrahydroborate; thionyl chloride; ethanol; sodium hydride; In tetrahydrofuran; mineral oil; 4: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acs.inorgchem.6b00972

upstream raw materials:

6-bromonicotinaldehyde

2-bromo-5-pyridylmethyl chloride

2-bromo-5-(hydroxymethyl)pyridine

4-dimethylamino-benzaldehyde

Downstream raw materials:

C₁₅H₁₈N₄