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

Base Information

• Chemical Name: α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide
• CAS No.: 365572-40-3
• Molecular Formula: C₁₈H₂₀BrNO₄
• Molecular Weight: 394.265
• Mol file: 365572-40-3.mol

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

Chemical Property of α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide

There total 9 articles about α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide 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: 99.0%

α-[2-bromo-4-methoxy-5-(1-methylethoxy)phenyl]4-(1-methylethoxy)benzenepentanamide (365572-39-0) → α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide (365572-40-3)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/jhet.5570390626

Reference yield:

4-hydroxyphenylpropionic acid (501-97-3) → α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide (365572-40-3)

Guidance literature:

Multi-step reaction with 7 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

7.1: 99 percent / BCl₃ / CH₂Cl₂ / -78 - 20 °C

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

DOI:10.1002/jhet.5570390626

Reference yield:

4-(1-methylethoxy)benzenepropanoic acid (1-methyl)ethyl ester (301224-94-2) → α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide (365572-40-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 12.5 h / 0 - 20 °C

2.1: 79 percent / iodine; imidazole; triphenylphosphine / CH₂Cl₂ / 12 h / 20 °C

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

3.2: 71 percent / tetrahydrofuran / 1 h / -78 °C

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

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

5.2: 26.0 g / NH₃ / tetrahydrofuran / 2 h

6.1: 99 percent / BCl₃ / CH₂Cl₂ / -78 - 20 °C

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

DOI:10.1002/jhet.5570390626

upstream raw materials:

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

4-hydroxyphenylpropionic acid

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

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

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.