α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide

Base Information

• Chemical Name: α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide
• CAS No.: 365572-39-0
• Molecular Formula: C₂₄H₃₂BrNO₄
• Molecular Weight: 478.426
• Mol file: 365572-39-0.mol

Synonyms:α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide

Chemical Property of α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide

There total 9 articles about α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide 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:

oxalyl dichloride (79-37-8) + α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanenitrile (365572-38-9) → α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide (365572-39-0)

Guidance literature:

With hydrogenchloride; potassium hydroxide; ammonia; In tetrahydrofuran; ethanol; di-isopropyl ether; water; N,N-dimethyl-formamide;

Reference yield:

2-(2-bromo-5-isopropoxy-4-methoxy-phenyl)-5-(4-isopropoxy-phenyl)-pentanoic acid → α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide (365572-39-0)

Guidance literature:

2-(2-bromo-5-isopropoxy-4-methoxy-phenyl)-5-(4-isopropoxy-phenyl)-pentanoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 2h;

With ammonia; In tetrahydrofuran; for 2h;

DOI:10.1002/jhet.5570390626

Reference yield:

4-hydroxyphenylpropionic acid (501-97-3) → α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide (365572-39-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 94 percent / potassium carbonate / dimethylformamide / 24 h / 60 °C

2.1: 99 percent / LiAlH₄ / tetrahydrofuran / 12.5 h / 0 - 20 °C

3.1: 79 percent / iodine; imidazole; triphenylphosphine / CH₂Cl₂ / 12 h / 20 °C

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / -78 - 20 °C

4.2: 71 percent / tetrahydrofuran / 1 h / -78 °C

5.1: aq. KOH / ethanol / 6 h / Heating

6.1: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 0 °C

6.2: 26.0 g / NH₃ / tetrahydrofuran / 2 h

With 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; iodine; potassium carbonate; diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570390626

upstream raw materials:

4-hydroxyphenylpropionic acid

4-(1-methylethoxy)benzenepropanoic acid (1-methyl)ethyl ester

1-bromo-2-(chloromethyl)-5-methoxy-4-(1-methylethoxy)benzene

1-(3-iodopropyl)-4-(1-methylethoxy)benzene

Downstream raw materials:

α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide

Refernces

• 1、 Treu, Matthias,Mereiter, Kurt,Hametner, Christian,Froehlich, Johannes,Jordis, Ulrich. "Carbocyclic galanthamin analogs: 4a,5,9,10,11,12-Hexahydro-6H-1283 benzo[b]cyclohepta[cd]benzofurans". . p. 1283 - 1288. Retrieved 2007/10/03.