methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 1245635-29-3
• Molecular Formula: C₁₄H₁₈BIO₅
• Molecular Weight: 404.009
• Mol file: 1245635-29-3.mol

Synonyms:methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property of methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 5 articles about methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)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:

2,3-dimethyl-2,3-butane diol (76-09-5) + [2-hydroxy-3-iodo-5-(methoxycarbonyl)phenyl]boronic acid (1245635-28-2) → methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1245635-29-3)

Guidance literature:

In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201002191

Reference yield:

[3-iodo-5-(methoxycarbonyl)-2-(methoxymethoxy)phenyl]boronic acid (1245635-27-1) → methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1245635-29-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: dichloromethane / 20 °C

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

DOI:10.1016/j.tet.2013.03.016

Reference yield:

methyl 4-hydroxy-3,5-diiodobenzoate (3337-66-4) → methyl 4-hydroxy-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1245635-29-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 3 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

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

DOI:10.1016/j.tet.2013.03.016

upstream raw materials:

2,3-dimethyl-2,3-butane diol

[2-hydroxy-3-iodo-5-(methoxycarbonyl)phenyl]boronic acid

methyl 4-hydroxy-3,5-diiodobenzoate

methyl 4-hydroxylbenzoate

Downstream raw materials:

methyl 3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethylsulfonyloxy)benzoate

methyl 3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(((2,4,5-trichlorophenyl)sulfonyl)oxy)benzoate

4-formyl-2-iodo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,4,5-trichlorobenzenesulfonate

5-((4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl)-1-methyl-1H-benzo[d]triazole