(E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

Base Information

• Chemical Name: (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol
• CAS No.: 1622307-88-3
• Molecular Formula: C₂₅H₁₈N₂O₃S
• Molecular Weight: 426.496

Synonyms:(E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

Chemical Property of (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

Chemical Property:

Purity/Quality:

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Technology Process of (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

There total 6 articles about (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol 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: 15.0%

3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (1622308-90-0) + tert-butyl 4-vinyl-1H-imidazole-1-carboxylate (1622309-48-1) → (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (1622307-88-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 150 ℃; for 1h; Microwave irradiation; Inert atmosphere;

Reference yield:

3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (1622308-83-1) → (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (1622307-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

2: boron tribromide / dichloromethane; hexane / 1 h / 20 °C

3: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; boron tribromide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3: |Heck Reaction;

Reference yield:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (1622307-88-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / 3 h / 0 - 20 °C

2.1: trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C

2.2: 1.5 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

3.2: 18 h / 80 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

5.1: boron tribromide / dichloromethane; hexane / 1 h / 20 °C

6.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; lithium aluminium tetrahydride; boron tribromide; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil; 6.1: |Heck Reaction;

upstream raw materials:

3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

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

3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

tert-butyl 4-vinyl-1H-imidazole-1-carboxylate

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