(E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane

Base Information

• Chemical Name: (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane
• CAS No.: 725230-29-5
• Molecular Formula: C₂₂H₃₇BrO₂Si
• Molecular Weight: 441.524
• Mol file: 725230-29-5.mol

Synonyms:(E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane

Chemical Property of (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane

There total 6 articles about (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane 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: 88.0%

(E)-4-[2-methoxy-3-methyl-5-(triisopropylsilyloxy)phenyl]-2-methylbut-2-en-1-ol (725230-51-3) → (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane (725230-29-5)

Guidance literature:

With bromine; 1,2-bis-(diphenylphosphino)ethane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200300767

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane (725230-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 10.7 g / potassium carbonate / acetone / 4 h / Heating

3.1: PhLi / dibutyl ether; cyclohexane / 1 h / 20 °C

3.2: 91 percent / DMPU / diethyl ether; cyclohexane / 12 h / 20 °C

4.1: selenium dioxide / dioxane; H₂O / 1 h / 100 °C

4.2: 60 percent / sodium borohydride / ethanol / 0.5 h / 20 °C

5.1: 88 percent / 1,2-bis(diphenylphosphanyl)ethane; bromine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; selenium(IV) oxide; bromine; potassium carbonate; phenyllithium; 1,2-bis-(diphenylphosphino)ethane; In 1,4-dioxane; dichloromethane; dibutyl ether; cyclohexane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.200300767

Reference yield:

2-bromo-6-methylbenzene-1,4-diol (50848-60-7) → (E)-[3-(4-bromo-3-methylbut-2-enyl)-4-methoxy-5-methylphenoxy]-triisopropylsilane (725230-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 10.7 g / potassium carbonate / acetone / 4 h / Heating

3.1: PhLi / dibutyl ether; cyclohexane / 1 h / 20 °C

3.2: 91 percent / DMPU / diethyl ether; cyclohexane / 12 h / 20 °C

4.1: selenium dioxide / dioxane; H₂O / 1 h / 100 °C

4.2: 60 percent / sodium borohydride / ethanol / 0.5 h / 20 °C

5.1: 88 percent / 1,2-bis(diphenylphosphanyl)ethane; bromine / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; selenium(IV) oxide; bromine; potassium carbonate; phenyllithium; 1,2-bis-(diphenylphosphino)ethane; In 1,4-dioxane; dichloromethane; dibutyl ether; cyclohexane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.200300767

upstream raw materials:

(E)-4-[2-methoxy-3-methyl-5-(triisopropylsilyloxy)phenyl]-2-methylbut-2-en-1-ol

triisopropylsilyl chloride

2-bromo-6-methylbenzene-1,4-diol

(3-bromo-4-methoxy-5-methylphenoxy)triisopropylsilane

Downstream raw materials:

(E)-2-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(2-methoxy-3-methyl-5-triisopropylsilanyloxy-phenyl)-2-methyl-but-2-enyl]-4-methyl-7-((R)-6,8,8-trimethyl-1,4,7-trioxa-spiro[4.5]dec-9-en-6-yl)-hept-3-enenitrile