4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile

Base Information

• Chemical Name: 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile
• CAS No.: 1176869-92-3
• Molecular Formula: C₃₈H₄₅NO₂SSi₂
• Molecular Weight: 636.018

Synonyms:4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile

Chemical Property of 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile

Chemical Property:

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Technology Process of 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile

There total 6 articles about 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile 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: 75.0%

4-{3-(3-methoxyphenyl)-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile (1176869-90-1) + 1-iodo-4-[[tris(1-methylethyl)silyl]oxy]benzene (180577-83-7) → 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile (1176869-92-3)

Guidance literature:

4-{3-(3-methoxyphenyl)-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile; With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; In tetrahydrofuran; at -20 ℃; for 12h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; at -20 ℃; for 0.5h; Inert atmosphere;

1-iodo-4-[[tris(1-methylethyl)silyl]oxy]benzene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1039/b907330b

Reference yield:

4-(3-(3-methoxyphenyl)-5-(trimethylsilyl)thiophen-2-yl)benzonitrile (1176869-86-5) → 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile (1176869-92-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Iodine monochloride / acetonitrile / 0 - 25 °C / Inert atmosphere

2.1: isopropylmagnesium bromide / tetrahydrofuran / 0.08 h / 60 °C / Inert atmosphere

2.2: 25 °C / Inert atmosphere

2.3: 2 h / 50 °C / Inert atmosphere

3.1: bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex / tetrahydrofuran / -20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

3.3: 3 h / 25 °C / Inert atmosphere

With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; isopropylmagnesium bromide; Iodine monochloride; In tetrahydrofuran; acetonitrile;

DOI:10.1002/chem.201003657

Reference yield:

4-[5-iodo-3-(3-methoxyphenyl)-2-thienyl]benzonitrile (1309446-64-7) → 4-{3-(3-methoxyphenyl)-4-{4-[(triisopropylsilyl)oxy]phenyl}-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile (1176869-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropylmagnesium bromide / tetrahydrofuran / 0.08 h / 60 °C / Inert atmosphere

1.2: 25 °C / Inert atmosphere

1.3: 2 h / 50 °C / Inert atmosphere

2.1: bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex / tetrahydrofuran / -20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: 3 h / 25 °C / Inert atmosphere

With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex; isopropylmagnesium bromide; In tetrahydrofuran;

DOI:10.1002/chem.201003657

upstream raw materials:

4-{3-(3-methoxyphenyl)-5-[(trimethylsilyl)ethynyl]-2-thienyl}benzonitrile

1-iodo-4-[[tris(1-methylethyl)silyl]oxy]benzene

{4-(3-methoxyphenyl)-5-[(4-methoxyphenyl)sulfinyl]-2-thienyl}(trimethyl)silane

4-(3-(3-methoxyphenyl)-5-(trimethylsilyl)thiophen-2-yl)benzonitrile

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