[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

Base Information

• Chemical Name: [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane
• CAS No.: 952156-26-2
• Molecular Formula: C₁₄H₂₅BrSi
• Molecular Weight: 301.342
• Mol file: 952156-26-2.mol

Synonyms:[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

Chemical Property of [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane

There total 2 articles about [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane 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: 80.0%

(E)-tert-butyldimethyl(2-tributylstannylvinyl)silane + 1-bromo-2-trifluoromethanesulfonyloxycyclohexene (213340-08-0) → [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane (952156-26-2) + (E)-1,2-bis[2-(tert-butyldimethylsilyl)vinyl]cyclohexene

Guidance literature:

With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 12h;

DOI:10.1002/ejoc.200700201

Reference yield:

2-bromocyclohexanone (1056477-06-5,822-85-5) → [(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane (952156-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium bis(trimethylsilyl)amide / diethyl ether / 0.5 h / -78 °C

1.2: 94 percent / diethyl ether / 24 h / -78 - 22 °C

2.1: 80 percent / LiCl / tetrakis(triphenylphosphane)palladium / dimethylformamide / 12 h / 90 °C

With potassium hexamethylsilazane; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; N,N-dimethyl-formamide; 2.1: Stille coupling;

DOI:10.1002/ejoc.200700201

Reference yield: 78.0%

[(E)-2-(2-bromocyclohex-1-enyl)vinyl]tert-butyldimethylsilane (952156-26-2) + tert-Butyl acrylate (1663-39-4,25232-27-3) → tert-butyl (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}acrylate (952156-32-0)

Guidance literature:

With triethylamine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 14h;

DOI:10.1002/ejoc.200700201

upstream raw materials:

1-bromo-2-trifluoromethanesulfonyloxycyclohexene

2-bromocyclohexanone

Downstream raw materials:

tert-butyl (E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}acrylate

(E)-3-{2'-[(E)-2-(tert-butyldimethylsilyl)vinyl]cyclohex-1'-enyl}prop-2-en-1-ol

(E)-tert-butyldimethyl(2-{(E)-2'-[3-(tetrahydropyran-2-yloxy)propenyl]cyclohex-1'-enyl}vinyl)silane