1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone

Base Information

• Chemical Name: 1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone
• CAS No.: 128260-43-5
• Molecular Formula: C₁₉H₂₂Br₂O₄
• Molecular Weight: 474.189
• Mol file: 128260-43-5.mol

Synonyms:1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone

Chemical Property of 1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone

There total 6 articles about 1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone 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%

Methanesulfonic acid 2,4-dibromo-6-[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-acetyl]-3,5-dimethoxy-phenyl ester (128260-46-8) → 1-(3,5-Dibromo-2-hydroxy-4,6-dimethoxy-phenyl)-2-[6,6-dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-ethanone (128260-43-5)

Guidance literature:

With NaCO₃; In ethanol;

DOI:10.1016/S0040-4039(00)70642-3

Reference yield: 74.0%

(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-4,6-dimethoxy-2-(methanesulfonyloxy)phenyl)ethanone (160618-31-5) → (E)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone (128260-43-5)

Guidance literature:

With sodium carbonate; In ethanol; at 70 ℃; for 0.333333h;

DOI:10.1021/jo00101a031

Reference yield:

Methanesulfonic acid 2,4-dibromo-6-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1-hydroxy-ethyl]-3,5-dimethoxy-phenyl ester → (E)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone (128260-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min; -78 deg C to 0 deg C, 2.) r.t., 90 min

2: 74 percent / Na₂CO₃ / aq. ethanol / 0.33 h / 70 °C

With oxalyl dichloride; sodium carbonate; dimethyl sulfoxide; triethylamine; In ethanol;

DOI:10.1021/jo00101a031

upstream raw materials:

Methanesulfonic acid 2,4-dibromo-6-[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-acetyl]-3,5-dimethoxy-phenyl ester

Methanesulfonic acid 2,4-dibromo-6-formyl-3,5-dimethoxy-phenyl ester

Methanesulfonic acid 2,4-dibromo-6-[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1-hydroxy-ethyl]-3,5-dimethoxy-phenyl ester

(1S)-(-)-β-pinene

Downstream raw materials:

(Z)-(1R)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ylidene)-1-(3,5-dibromo-2-hydroxy-4,6-dimethoxyphenyl)ethanone