3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

Base Information

Chemical Name:3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde
CAS No.:959996-47-5
Molecular Formula:C₁₆H₂₀BrFN₂O₂Si
Molecular Weight:399.335
Hs Code.:

Synonyms:3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

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Chemical Property of 3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

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Technology Process of 3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

There total 5 articles about 3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde 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: 73.0%

: 959996-48-6
2-bromo-5-fluorobenzeneboronic acid

: 959996-42-0
3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-carbaldehyde

: 959996-47-5
3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

Guidance literature:: With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 80 ℃; for 18h;

Reference yield:

: 827316-45-0
3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-carboxylic acid ethyl ester

: 959996-47-5
3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydroxide / 96 h

2.1: dimethylsulfide borane complex / tetrahydrofuran / 19 h / 0 - 50 °C

2.2: 0.5 h

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 24 h

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dimethylsulfide borane complex; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1021/jm301741t

Reference yield:

: 202865-72-3
1-bromo-4-fluoro-2-iodobenzene

: 959996-47-5
3-(2-bromo-5-fluorophenyl)-1-(2-trimethylsilylethoxymethyl)pyrazole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -42 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

1.3: 1 h / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylmagnesium chloride; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water;
DOI:10.1021/jm301741t