4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

Base Information

Chemical Name:4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde
CAS No.:635679-16-2
Molecular Formula:C₂₂H₁₄O₂S
Molecular Weight:342.418
Hs Code.:

Synonyms:4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

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Chemical Property of 4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

Chemical Property:

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Technology Process of 4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

There total 8 articles about 4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde 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:

: 635679-15-1
2-hydroxy-4-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-benzaldehyde

: 635679-16-2
4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1002/anie.200352075

Reference yield:

: 18278-34-7
4-hydroxy-2-methoxybenzaldehyde

: 635679-16-2
4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / pyridine

2: 79 percent / BBr₃ / CH₂Cl₂ / -40 °C

3: 64 percent / triethylamine / [Pd(PPh₃)4] / dimethylformamide / 24 h / 100 °C

4: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; boron tribromide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200352075

Reference yield:

: 123568-21-8
2,5-Dibromo-4-iodotoluene

: 635679-16-2
4-[5-(2,5-diethynyl-4-methyl-phenyl)-thiophen-2-yl]-2-hydroxy-benzaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 76 percent / [PdCl₂(PPh₃)2] / dimethylformamide / 12 h / 80 °C

2.1: 76 percent / CuI; diisopropylamine / [Pd(PPh₃)4] / toluene / 20 h / 80 °C

3.1: tBuLi / tetrahydrofuran / 1.5 h / -70 °C

3.2: 59 percent / tetrahydrofuran / 4 h / 20 °C

4.1: 64 percent / triethylamine / [Pd(PPh₃)4] / dimethylformamide / 24 h / 100 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; tert.-butyl lithium; triethylamine; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Stille cross-coupling / 2.1: Sonogashira cross-coupling;
DOI:10.1002/anie.200352075