N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide

Base Information

• Chemical Name: N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide
• CAS No.: 1420013-23-5
• Molecular Formula: C₁₆H₂₂BrNO₂Si
• Molecular Weight: 368.346
• Mol file: 1420013-23-5.mol

Synonyms:N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide

Chemical Property of N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide

There total 9 articles about N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide 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: 46.0%

3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) + C10H10BrNO2 (1420013-02-0) → N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide (1420013-23-5)

Guidance literature:

3-bromo-1-(trimethylsilyl)-1-propyne; With indium; indium(III) bromide; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

C₁₀H₁₀BrNO₂; In tetrahydrofuran; at 80 ℃; Inert atmosphere;

DOI:10.1021/ja3121394

Reference yield:

N-(2-bromo-3-(2-methoxyvinyl)phenyl)acetamide (1420013-09-7) → N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide (1420013-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: indium(III) bromide; indium / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

2.2: 80 °C / Inert atmosphere

With hydrogenchloride; indium; indium(III) bromide; In tetrahydrofuran;

DOI:10.1021/ja3121394

Reference yield:

2-bromo-3-nitro-benzoic acid (573-54-6) → N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide (1420013-23-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: borane-THF / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.1: acetic acid; iron; hydrogenchloride / ethanol / 3 h / 100 °C

3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

6.1: manganese(IV) oxide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

7.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

7.2: 0.25 h / Inert atmosphere

8.1: hydrogenchloride / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: indium(III) bromide; indium / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

9.2: 80 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; indium; borane-THF; indium(III) bromide; potassium tert-butylate; tetrabutyl ammonium fluoride; iron; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja3121394

upstream raw materials:

2-bromo-3-nitro-benzoic acid

2-bromo-3-(hydroxymethyl)-1-nitrobenzene

3-bromo-1-(trimethylsilyl)-1-propyne

C₁₀H₁₀BrNO₂

Downstream raw materials:

rac-9,10-dihydrolysergol

rac-9,10-dihydrolysergic acid

methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate