ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate

Base Information

• Chemical Name: ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate
• CAS No.: 1440955-95-2
• Molecular Formula: C₂₁H₃₃BO₅
• Molecular Weight: 376.301
• Mol file: 1440955-95-2.mol

Synonyms:ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate

Chemical Property of ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate

There total 4 articles about ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate 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: 49.0%

ethyl 4-((5-bromopentyl)oxy)benzoate (96517-13-4) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate (1440955-95-2)

Guidance literature:

4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane; With copper(l) iodide; lithium tert-butoxide; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

ethyl 4-((5-bromopentyl)oxy)benzoate; In N,N-dimethyl-formamide; at 60 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol503111h

Reference yield:

bis(pinacol)diborane (73183-34-3) → ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate (1440955-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium methanolate; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 40 °C / Schlenk technique; Inert atmosphere

2.1: lithium tert-butoxide; copper(l) iodide / N,N-dimethyl-formamide / 0.17 h / 20 - 60 °C / Inert atmosphere; Schlenk technique

2.2: 24 h / 60 °C / Inert atmosphere; Schlenk technique

With copper(l) iodide; lithium methanolate; lithium tert-butoxide; In N,N-dimethyl-formamide; 2.1: |Suzuki-Miyaura Coupling / 2.2: |Suzuki-Miyaura Coupling;

DOI:10.1021/ol503111h

Reference yield:

Ethyl 4-hydroxybenzoate (120-47-8) + 1,5-dibromo-pentane (111-24-0) → ethyl 4-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexyl)oxy)benzoate (1440955-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere; Schlenk technique

1.2: Inert atmosphere; Schlenk technique

2.1: lithium tert-butoxide; copper(l) iodide / N,N-dimethyl-formamide / 0.17 h / 20 - 60 °C / Inert atmosphere; Schlenk technique

2.2: 24 h / 60 °C / Inert atmosphere; Schlenk technique

With copper(l) iodide; potassium carbonate; lithium tert-butoxide; In N,N-dimethyl-formamide; 2.1: |Suzuki-Miyaura Coupling / 2.2: |Suzuki-Miyaura Coupling;

DOI:10.1021/ol503111h

upstream raw materials:

6-(4-carbethoxyphenoxy)hexyl bromide

bis(pinacol)diborane

Ethyl 4-hydroxybenzoate

1,5-dibromo-pentane

Downstream raw materials:

6-(4-(ethoxycarbonyl)phenoxy)hexylboronic acid