3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

Base Information

Chemical Name:3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol
CAS No.:1448888-97-8
Molecular Formula:C₂₅H₂₉BrO₅Si
Molecular Weight:517.492
Hs Code.:

Synonyms:3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

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Chemical Property of 3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

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Technology Process of 3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

There total 8 articles about 3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 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: 98.0%

: 1448888-95-6
((Z)-4-(2-bromo-3-((5-iodobenzo[d][1,3]dioxol-4-yl)methoxy)-4-methoxyphenyl)but-2-en-1-yl)trimethylsilane

: 107-19-7
propargyl alcohol

: 1448888-97-8
3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium acetate; In 1,4-dioxane; at 60 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/anie.201209868

Reference yield:

: 5876-51-7
5-iodo-1,3-benzodioxole

: 1448888-97-8
3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 18 h / -78 °C / Inert atmosphere

2.1: sodium tetrahydroborate / ethanol / 0 - 20 °C / Inert atmosphere

3.1: phosphorus tribromide / dichloromethane / 18 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / acetonitrile / 5 h / 80 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium acetate; copper(l) iodide / 1,4-dioxane / 0.5 h / 60 °C / Inert atmosphere

With sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium acetate; phosphorus tribromide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; acetonitrile; 5.1: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201209868

Reference yield:

: 249636-72-4
5-iodobenzo[d][1,3]dioxole-4-carbaldehyde

: 1448888-97-8
3-(4-((2-bromo-6-methoxy-3-((Z)-4-(trimethylsilyl)but-2-en-1-yl)phenoxy)methyl)benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate / ethanol / 0 - 20 °C / Inert atmosphere

2: phosphorus tribromide / dichloromethane / 18 h / 20 °C / Inert atmosphere

3: potassium carbonate / acetonitrile / 5 h / 80 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium acetate; copper(l) iodide / 1,4-dioxane / 0.5 h / 60 °C / Inert atmosphere

With sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammonium acetate; phosphorus tribromide; potassium carbonate; In 1,4-dioxane; ethanol; dichloromethane; acetonitrile; 4: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201209868