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

Base Information

• Chemical Name: methyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 1352730-33-6
• Molecular Formula: C₁₄H₁₉BO₅
• Molecular Weight: 278.113
• Mol file: 1352730-33-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-Hydroxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about methyl 2-hydroxy-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: 91.0%

5-bromo-2-hydroxy-benzoic acid methyl ester (4068-76-2) + bis(pinacol)diborane (73183-34-3) → methyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1352730-33-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; for 18h; Inert atmosphere; Reflux;

DOI:10.1021/jacs.1c04030

Reference yield:

methyl 5-iodosalicylate (4068-75-1) + bis(pinacol)diborane (73183-34-3) → methyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1352730-33-6)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos; In 1,4-dioxane; at 110 ℃;

DOI:10.1016/j.bmc.2020.115794

Reference yield:

5-bromosalicyclic acid (89-55-4) → methyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1352730-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 12 h / Reflux

2: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 24 h / Inert atmosphere; Reflux

With bis-triphenylphosphine-palladium(II) chloride; sulfuric acid; potassium acetate; In 1,4-dioxane;

DOI:10.1021/jacs.7b13825

upstream raw materials:

5-bromo-2-hydroxy-benzoic acid methyl ester

bis(pinacol)diborane

5-bromosalicyclic acid

methyl 5-iodosalicylate

Downstream raw materials:

4,4’-dihydroxy-(1,1’-biphenyl)-3,3’-dicarboxylic acid

4,4′′-dihydroxy-[1,1′:4′,1′′-terphenyl]-3,3′′-dicarboxylic acid

Refernces

• 1、 Cotrina, Ellen Y.,Blasi, Daniel,Vilà, Marta,Planas, Antoni,Abad-Zapatero, Cele,Centeno, Nuria B.,Quintana, Jordi,Arsequell, Gemma. "Optimization of kinetic stabilizers of tetrameric transthyretin: A prospective ligand efficiency-guided approach". . . Retrieved 2020.
• 2、 Qiu, Jin,Zhao, Baobing,Zhong, Wanxia,Shen, Yuemao,Lin, Houwen. "Synthesis, biological evaluation and modeling studies of terphenyl topoisomerase II α inhibitors as anticancer agents". . p. 427 - 435. Retrieved 2015/03/30.