2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol

Base Information

• Chemical Name: 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol
• CAS No.: 171888-42-9
• Molecular Formula: C₂₀H₁₈Cl₂O₃S
• Molecular Weight: 409.333
• Mol file: 171888-42-9.mol

Synonyms:2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol

Chemical Property of 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol

There total 14 articles about 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol 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:

C34H32Cl2O9S3 → 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol (171888-42-9)

Guidance literature:

With sodium iodide; zinc; In N,N-dimethyl-formamide; at 150 ℃; for 3h;

DOI:10.1021/jm950664x

Reference yield:

3,5-dichloro-4-hydroxybenzoic acid (3336-41-2) → 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol (171888-42-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) K₂CO₃, 2.) 2.5 N NaOH / 1.) DMF, 55 deg C, 1 8 h, 2.) methanol, reflux, 4 h

2: 1.) thionyl chloride, 2.) triethylamine / 1.) DMF, reflux, 4 h, 2.) RT, overnight

3: methylmagnesium bromide / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature

4: conc. HCl, bromine / acetic acid / 2 h / Ambient temperature

5: K₂CO₃, KI / tetrahydrofuran

6: TiCl₃, zinc dust / 1,2-dimethoxy-ethane / 1 h / Heating

7: DIBAL / tetrahydrofuran / 0.25 h / -78 °C

8: pyridine / Ambient temperature

9: NaI, zinc dust / dimethylformamide / 3 h / 150 °C

With pyridine; hydrogenchloride; sodium hydroxide; thionyl chloride; titanium(III) chloride; methylmagnesium bromide; bromine; diisobutylaluminium hydride; potassium carbonate; triethylamine; potassium iodide; sodium iodide; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm950664x

Reference yield:

2-bromo-1-(4-methanesulfonylphenyl)ethanone (50413-24-6) → 2,6-Dichloro-4-[6-(4-methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-phenol (171888-42-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 63.3 percent / K₂CO₃, KI / tetrahydrofuran / 6 h / Ambient temperature

2: K₂CO₃, KI / tetrahydrofuran

3: TiCl₃, zinc dust / 1,2-dimethoxy-ethane / 1 h / Heating

4: DIBAL / tetrahydrofuran / 0.25 h / -78 °C

5: pyridine / Ambient temperature

6: NaI, zinc dust / dimethylformamide / 3 h / 150 °C

With pyridine; titanium(III) chloride; diisobutylaluminium hydride; potassium carbonate; potassium iodide; sodium iodide; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jm950664x

upstream raw materials:

3,5-dichloro-4-hydroxybenzoic acid

2-bromo-1-(4-methanesulfonylphenyl)ethanone

4-(Methylthio)acetophenone

4-(methanesulfonyl)acetophenone

Downstream raw materials:

5-(3,5-dichloro-4-methoxyphenyl)-6-[4-(methylsulfonyl)phenyl]spiro[2.4]hept-5-ene