(Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone

Base Information

• Chemical Name: (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone
• CAS No.: 350037-73-9
• Molecular Formula: C₁₀H₁₃BrO
• Molecular Weight: 229.117
• Mol file: 350037-73-9.mol

Synonyms:(Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone

Chemical Property of (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone

There total 5 articles about (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone 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: 71.0%

2-(2,2-dibromovinyl)-4,4-dimethylcyclohex-2-enone (350037-74-0) → (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone (350037-73-9)

Guidance literature:

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200105)2001:9<1619::AID-EJOC1619>3.0.CO;2-T

Reference yield:

4,4-dimethylcyclohexenone (1073-13-8) → (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone (350037-73-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / H₂ / Pd/C / pentane / 24 h

2: 94 percent / NaH / cyclohexane / 4 h / Heating

3: 76 percent / DDQ / dioxane / 0.08 h / 20 °C

4: 79 percent / PPh₃ / CH₂Cl₂ / 2.5 h / 0 - 20 °C

5: 71 percent / nBu₃SnH / Pd(PPh₃)4 / toluene / 2 h / 20 °C

With hydrogen; tri-n-butyl-tin hydride; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; cyclohexane; toluene; pentane; 2: Claisen condensation / 4: Corey-Fuchs reaction;

DOI:10.1002/1099-0690(200105)2001:9<1619::AID-EJOC1619>3.0.CO;2-T

Reference yield:

4,4-dimethylcyclohexane-1-one (4255-62-3) → (Z)-2-(2-bromovinyl)-4,4-dimethylcyclohex-2-enone (350037-73-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / NaH / cyclohexane / 4 h / Heating

2: 76 percent / DDQ / dioxane / 0.08 h / 20 °C

3: 79 percent / PPh₃ / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4: 71 percent / nBu₃SnH / Pd(PPh₃)4 / toluene / 2 h / 20 °C

With tri-n-butyl-tin hydride; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; cyclohexane; toluene; 1: Claisen condensation / 3: Corey-Fuchs reaction;

DOI:10.1002/1099-0690(200105)2001:9<1619::AID-EJOC1619>3.0.CO;2-T

upstream raw materials:

2-(2,2-dibromovinyl)-4,4-dimethylcyclohex-2-enone

4,4-dimethylcyclohexenone

4,4-dimethylcyclohexane-1-one

5,5-dimethyl-2-oxocyclohexane-1-carbaldehyde

Downstream raw materials:

(Z)-2-{2-[(1R,3aS,4S,7aS)-1-tert-butoxy-2,3,3a,4,7,7a-hexahydro-7a-methyl-1H-indole-4-yl]vinyl}-4,4-dimethylcyclohex-2-enone