Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester

Base Information

• Chemical Name: Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester
• CAS No.: 431874-74-7
• Molecular Formula: C₁₃H₁₇BrO₂
• Molecular Weight: 285.181
• Mol file: 431874-74-7.mol

Synonyms:Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester

Chemical Property of Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester

There total 3 articles about Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester 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: 81.0%

acryloyl chloride (814-68-6,25189-84-8) + (Z)-(S)-4-Bromo-4-cyclohex-1-enyl-but-3-en-2-ol (431874-78-1) → Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester (431874-74-7)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1021/ol0259746

Reference yield:

((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane (431874-77-0) → Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester (431874-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

2: 81 percent / triethylamine / CH₂Cl₂ / 0.5 h / 25 °C

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0259746

Reference yield:

cyclohex-1-enylboronic acid (89490-05-1,21190-87-4) → Acrylic acid (Z)-(S)-3-bromo-3-cyclohex-1-enyl-1-methyl-allyl ester (431874-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; Ba(OH)2 / tetrahydrofuran; methanol; H₂O / 15 h / 20 °C

2: 94 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

3: 81 percent / triethylamine / CH₂Cl₂ / 0.5 h / 25 °C

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Suzuki-Miyaura coupling;

DOI:10.1021/ol0259746

upstream raw materials:

acryloyl chloride

(Z)-(S)-4-Bromo-4-cyclohex-1-enyl-but-3-en-2-ol

((Z)-(S)-3-Bromo-3-cyclohex-1-enyl-1-methyl-allyloxy)-tert-butyl-dimethyl-silane

cyclohex-1-enylboronic acid