rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate

Base Information

• Chemical Name: rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate
• CAS No.: 934170-59-9
• Molecular Formula: C₁₆H₁₇BrO₄
• Molecular Weight: 353.213
• Mol file: 934170-59-9.mol

Synonyms:rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate

Chemical Property of rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate

There total 4 articles about rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate 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: 94.0%

C10H14O3 + rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-en-1-ol (934170-57-7) → rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate (934170-59-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.3987/com-06-s(w)42

Reference yield:

2-bromo-3,6-dimethoxybenzaldehyde (85432-87-7) → rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate (934170-59-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / tetrahydrofuran

2: 94 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 °C

With lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.3987/com-06-s(w)42

Reference yield:

2-bromo-3,6-dihydroxy-benzaldehyde (241127-72-0) → rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-enyl cyclobut-1-enecarboxylate (934170-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C

2.1: tetrahydrofuran / 0.67 h / -78 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

With sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.7b03268

upstream raw materials:

rac-1-(2-bromo-3,6-dimethoxyphenyl)prop-2-en-1-ol

2-bromo-3,6-dimethoxybenzaldehyde

2-bromo-3,6-dihydroxy-benzaldehyde

1-cyclobutenecarboxylic acid

Downstream raw materials:

rac-5-(2-bromo-3,6-dimethoxyphenyl)-3-(but-3-enyl)-5H-furan-2-one

3-but-3-enyl-5-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-5H-furan-2-one