6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid

Base Information

• Chemical Name: 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid
• CAS No.: 1586025-49-1
• Molecular Formula: C₂₁H₂₁NO₅S
• Molecular Weight: 399.467

Synonyms:6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid

Chemical Property of 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid

Chemical Property:

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Technology Process of 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid

There total 5 articles about 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid 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: 72.0%

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate (1586025-47-9) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid (1586025-49-1)

Guidance literature:

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate; With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 5h; Inert atmosphere;

With hydrogenchloride; In dichloromethane; water; Inert atmosphere;

DOI:10.1002/cmdc.201300270

Reference yield:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid (1586025-49-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bromine / chloroform / 0.17 h / 50 °C / Inert atmosphere

2.1: n-butyllithium / hexane / 2 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: Inert atmosphere

3.1: thionyl chloride / toluene / 2 h / Reflux; Inert atmosphere

4.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

With n-butyllithium; thionyl chloride; bromine; boron tribromide; triethylamine; In hexane; dichloromethane; chloroform; toluene;

DOI:10.1002/cmdc.201300270

Reference yield:

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate (186787-88-2) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoic acid (1586025-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

With boron tribromide; triethylamine; In dichloromethane;

DOI:10.1002/cmdc.201300270

upstream raw materials:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

Downstream raw materials:

methyl 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

6-hydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamide

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