4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol

Base Information

• Chemical Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol
• CAS No.: 1542755-56-5
• Molecular Formula: C₂₃H₂₅BO₃
• Molecular Weight: 360.261
• Mol file: 1542755-56-5.mol

Synonyms:4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol

Chemical Property of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol

There total 6 articles about 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)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: 53.0%

4-Bromo-2-((naphthalen-2-yl)methyl)phenol (1542755-38-3) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol (1542755-56-5)

Guidance literature:

4-Bromo-2-((naphthalen-2-yl)methyl)phenol; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 2h; Inert atmosphere;

bis(pinacol)diborane; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2013.10.051

Reference yield:

β-naphthaldehyde (66-99-9) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol (1542755-56-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium; iodine / tetrahydrofuran / 6.17 h / Sealed tube; Inert atmosphere; Reflux

1.2: 20 °C / Sealed tube; Inert atmosphere

2.1: trifluoroacetic acid; triethylsilane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 20 °C

4.1: tetra-n-butylammonium tribromide / chloroform / 20 °C

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

5.2: 80 °C / Inert atmosphere

With triethylsilane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra-n-butylammonium tribromide; iodine; potassium acetate; boron tribromide; sodium hydrogencarbonate; magnesium; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; 5.1: |Miyaura Borylation Reaction;

DOI:10.1016/j.bmc.2013.10.051

Reference yield:

(2-methoxyphenyl)(naphthalen-2-yl)methanol → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-((naphthalen-2-yl)methyl)phenol (1542755-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid; triethylsilane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 20 °C

3.1: tetra-n-butylammonium tribromide / chloroform / 20 °C

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

4.2: 80 °C / Inert atmosphere

With triethylsilane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra-n-butylammonium tribromide; potassium acetate; boron tribromide; sodium hydrogencarbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; chloroform; 4.1: |Miyaura Borylation Reaction;

DOI:10.1016/j.bmc.2013.10.051

upstream raw materials:

β-naphthaldehyde

2-(2-methoxybenzyl)naphthalene

2-((naphthalen-2-yl)methyl)phenol

4-Bromo-2-((naphthalen-2-yl)methyl)phenol

Downstream raw materials:

ethyl 2-(1,1'-biphenyl-3'-(naphthalen-2-yl)methyl-4'-ol-4-oxy) acetate