4-ethynyl-5-iodophthalic acid dimethyl ester

Base Information

• Chemical Name: 4-ethynyl-5-iodophthalic acid dimethyl ester
• CAS No.: 1352007-55-6
• Molecular Formula: C₁₂H₉IO₄
• Molecular Weight: 344.106
• Mol file: 1352007-55-6.mol

Synonyms:

Chemical Property of 4-ethynyl-5-iodophthalic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-ethynyl-5-iodophthalic acid dimethyl ester

There total 5 articles about 4-ethynyl-5-iodophthalic acid dimethyl 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:

C15H17IO4Si → 4-ethynyl-5-iodophthalic acid dimethyl ester (1352007-55-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -15 ℃; for 0.5h;

DOI:10.1021/jo202016v

Reference yield:

o-xylene (95-47-6) → 4-ethynyl-5-iodophthalic acid dimethyl ester (1352007-55-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium periodate; sulfuric acid; iodine / water / 70 °C

2.1: pyridine; potassium permanganate / water / 48 h / Reflux

2.2: Heating

2.3: pH 1 - 2

3.1: thionyl chloride / 20 °C

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / -15 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium permanganate; sodium periodate; copper(l) iodide; thionyl chloride; sulfuric acid; tetrabutyl ammonium fluoride; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; water; 4.1: Sonogashira coupling;

DOI:10.1021/jo202016v

Reference yield:

1,2-diiodo-4,5-dimethyl-benzene (5182-67-2) → 4-ethynyl-5-iodophthalic acid dimethyl ester (1352007-55-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; potassium permanganate / water / 48 h / Reflux

1.2: Heating

1.3: pH 1 - 2

2.1: thionyl chloride / 20 °C

3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / -15 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium permanganate; copper(l) iodide; thionyl chloride; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; water; 3.1: Sonogashira coupling;

DOI:10.1021/jo202016v

upstream raw materials:

o-xylene

1,2-diiodo-4,5-dimethyl-benzene

dimethyl 4,5-diiodo-1,2-benzenedicarboxylate

4,5-diiodobenzene-1,2-dicarboxylic acid

Downstream raw materials:

tetramethyl 4,4'-ethyne-1,2-diylbis(5-iodobenzene-1,2-di-carboxylate)

tetramethyl 5,5'-(4,5-bis(methoxycarbonyl)-1,2-phenylene)bis(ethyne-2,1-diyl)bis(4-iodophthalate)

Refernces