2-methyl-phenylethynylboronic acid MIDA ester

Base Information

• Chemical Name: 2-methyl-phenylethynylboronic acid MIDA ester
• CAS No.: 1237789-57-9
• Molecular Formula: C₁₄H₁₄BNO₄
• Molecular Weight: 271.08
• Mol file: 1237789-57-9.mol

Synonyms:2-methyl-phenylethynylboronic acid MIDA ester

Chemical Property of 2-methyl-phenylethynylboronic acid MIDA ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 2-methyl-phenylethynylboronic acid MIDA ester

There total 2 articles about 2-methyl-phenylethynylboronic acid MIDA ester 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: 93.0%

ortho-methylphenyl iodide (615-37-2) + B-ethynyl N-methyliminodiacetic acid boronate (1104637-53-7) → 2-methyl-phenylethynylboronic acid MIDA ester (1237789-57-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 30 ℃; for 1h; Inert atmosphere; Sealed tube;

DOI:10.3762/bjoc.12.187

Reference yield:

N-methyliminodiacetic acid (4408-64-4) → 2-methyl-phenylethynylboronic acid MIDA ester (1237789-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 4 h / -78 - 20 °C

1.2: 130 °C

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: |Sonogashira Cross-Coupling;

DOI:10.1039/c9cc08386c

Reference yield: 96.0%

1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione (2232-12-4) + 2-methyl-phenylethynylboronic acid MIDA ester (1237789-57-9) + triethylamine tris(hydrogen fluoride) (73602-61-6,23588-89-8,29585-72-6,94527-74-9) → C14H14BFINO4

Guidance literature:

In dichloromethane; at 20 ℃; for 0.333333h; regioselective reaction; Sealed tube;

DOI:10.1039/c9cc08386c

upstream raw materials:

ortho-methylphenyl iodide

B-ethynyl N-methyliminodiacetic acid boronate

N-methyliminodiacetic acid

Refernces

• 1、 Wilson, Kirsty L.,Kennedy, Alan R.,Murray, Jane,Greatrex, Ben,Jamieson, Craig,Watson, Allan J. B.. "Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation". supporting information. p. 2005 - 2011. Retrieved 2016/10/05.