2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene

Base Information

• Chemical Name: 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene
• CAS No.: 1245635-00-0
• Molecular Formula: C₂₅H₃₀BNO₄S
• Molecular Weight: 451.394
• Mol file: 1245635-00-0.mol

Synonyms:2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene

Chemical Property of 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene

There total 7 articles about 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene 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:

2-Iodo-4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate (1245635-20-4) + 3-methyl-1-(4-methylbenzenesulphonyl)-1H-pyrrole (153633-33-1) → 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene (1245635-00-0) + C25H30BNO4S (1245635-54-4)

Guidance literature:

With TurboGrignard; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.583333h; Overall yield = 87 %; Overall yield = 40 mg; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.016

Reference yield:

2,6-diiodo-4-methylphenol (2432-18-0) → 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene (1245635-00-0) + C25H30BNO4S (1245635-54-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 5 h / 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 0 - 20 °C

4.1: dichloromethane / 20 °C

5.1: pyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

6.1: TurboGrignard / tetrahydrofuran; diethyl ether / 0.58 h / -78 °C / Inert atmosphere

With pyridine; TurboGrignard; n-butyllithium; chloro-trimethyl-silane; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile; 6.1: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2013.03.016

Reference yield:

[3-iodo-2-(methoxymethoxy)-5-methylphenyl]boronic acid (1245635-17-9) → 2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-tosyl-1,4-dihydro-1,4-epiminonaphthalene (1245635-00-0) + C25H30BNO4S (1245635-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 0 - 20 °C

2: dichloromethane / 20 °C

3: pyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

4: TurboGrignard / tetrahydrofuran; diethyl ether / 0.58 h / -78 °C / Inert atmosphere

With pyridine; TurboGrignard; chloro-trimethyl-silane; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 4: |Diels-Alder Cycloaddition;

DOI:10.1016/j.tet.2013.03.016

upstream raw materials:

1,3-diiodo-2-(methoxymethoxy)-5-methylbenzene

2,6-diiodo-4-methylphenol

[3-iodo-2-(methoxymethoxy)-5-methylphenyl]boronic acid

(2-hydroxy-3-iodo-5-methylphenyl)boronic acid