4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate

Base Information

• Chemical Name: 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate
• CAS No.: 1245635-25-9
• Molecular Formula: C₁₃H₁₄BBrF₃IO₅S
• Molecular Weight: 556.932

Synonyms:4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate

Chemical Property of 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

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Technology Process of 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate

There total 6 articles about 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate 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:

trifluoromethylsulfonic anhydride (358-23-6) + 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1245635-24-8) → 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate (1245635-25-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1002/anie.201002191

Reference yield:

2,6-di-iodo-4-bromophenol (15459-51-5) → 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate (1245635-25-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere

2.1: isopropylmagnesium chloride / tetrahydrofuran / 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 / 3.5 h / 0 °C / Inert atmosphere

With pyridine; chloro-trimethyl-silane; isopropylmagnesium chloride; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2013.03.016

Reference yield:

[5-bromo-3-iodo-2-(methoxymethoxy)phenyl]boronic acid (1245635-22-6) → 4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate (1245635-25-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: dichloromethane / 20 °C

3: pyridine / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With pyridine; chloro-trimethyl-silane; sodium iodide; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2013.03.016

upstream raw materials:

trifluoromethylsulfonic anhydride

4-bromo-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

2,6-di-iodo-4-bromophenol

4-bromo-phenol

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