6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol

Base Information

• Chemical Name: 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol
• CAS No.: 76042-41-6
• Molecular Formula: C₂₀H₁₉BrOS
• Molecular Weight: 387.34
• Mol file: 76042-41-6.mol

Synonyms:6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol

Chemical Property of 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol

There total 8 articles about 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol 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: 70.0%

2-<(1-((2,6-dimethoxyphenyl)thio)cyclopropyl)methylene>-6-bromo-3,4-dihydronaphthalen-1-one (76042-26-7) → 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol (76042-41-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1021/ja00547a015

Reference yield:

2,6-dimethoxybenzenethiol (26163-11-1) → 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol (76042-41-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / potassium carbonate / methanol; H₂O / 3 h

2: 90 percent / lithium diisopropylamide, HMPA / tetrahydrofuran / -78 deg C -> room temperature, overnight

3: 1.) DIBAL-H, 2.) 6percent aq. sulfuric acid / 1.) toluene, hexane, 0 deg C, 3 h, 2.) room temperature, 1 h

4: lithium diisopropylamide, anhydrous zinc chloride / tetrahydrofuran; diethyl ether / -10 °C

5: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

6: 70 percent / DIBAL-H / tetrahydrofuran; hexane / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sulfuric acid; diisobutylaluminium hydride; potassium carbonate; zinc(II) chloride; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; methanol; diethyl ether; hexane; water;

DOI:10.1021/ja00547a015

Reference yield:

1-((2,6-dimethoxyphenyl)thio)cyclopropane-1-carboxaldehyde (76042-16-5) → 6-Bromo-2-[1-(1-phenylsulfanyl-cyclopropyl)-meth-(E)-ylidene]-1,2,3,4-tetrahydro-naphthalen-1-ol (76042-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium diisopropylamide, anhydrous zinc chloride / tetrahydrofuran; diethyl ether / -10 °C

2: 1.) phosphorus oxychloride, HMPA, 2.) pyridine / 1.) room temperature -> 50 deg C, 2.) 50 deg C -> 100 deg C

3: 70 percent / DIBAL-H / tetrahydrofuran; hexane / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diisobutylaluminium hydride; zinc(II) chloride; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ja00547a015

upstream raw materials:

2-<(1-((2,6-dimethoxyphenyl)thio)cyclopropyl)methylene>-6-bromo-3,4-dihydronaphthalen-1-one

2,6-dimethoxybenzenethiol

((2,6-dimethoxyphenyl)thio)acetonitrile

1-((2,6-dimethoxyphenyl)thio)cyclopropane-1-carboxaldehyde