(S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran

Base Information

• Chemical Name: (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran
• CAS No.: 511270-20-5
• Molecular Formula: C₁₇H₂₃BrO₅Si
• Molecular Weight: 415.356
• Mol file: 511270-20-5.mol

Synonyms:(S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran

Chemical Property of (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran

There total 4 articles about (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran 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:

2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenol (225917-81-7) + 2-tert-butoxycarbonyloxy-5-oxo-2,5-dihydrofuran (225917-67-9) → (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran (511270-20-5) + (R)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran

Guidance literature:

With caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In dichloromethane; at 20 ℃; for 16h; Title compound not separated from byproducts.;

DOI:10.1021/ja020988s

Reference yield:

5-methoxyresorcinol (2174-64-3) → (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran (511270-20-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 48 percent / 2,4,4,6-tetrabromodienone / CHCl₃; dioxane / 5 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.33 h / 20 °C

2.2: 50 percent / tetrahydrofuran / 1 h / 20 °C

3.1: cesium carbonate; (R,R)-1,2-(Ph₂P-o-C₆H₄-CONH)2-cyclohexane / Pd₂dba3*CHCl₃ / CH₂Cl₂ / 16 h / 20 °C

With sodium hydride; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform;

DOI:10.1021/ja020988s

Reference yield:

2-bromo-5-methoxybenzene-1,3-diol (121869-51-0) → (S)-2-[2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenoxy]-5-oxo-2,5-dihydrofuran (511270-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.33 h / 20 °C

1.2: 50 percent / tetrahydrofuran / 1 h / 20 °C

2.1: cesium carbonate; (R,R)-1,2-(Ph₂P-o-C₆H₄-CONH)2-cyclohexane / Pd₂dba3*CHCl₃ / CH₂Cl₂ / 16 h / 20 °C

With sodium hydride; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja020988s

upstream raw materials:

2-bromo-3-(tert-butyldimethylsiloxy)-5-methoxyphenol

2-tert-butoxycarbonyloxy-5-oxo-2,5-dihydrofuran

5-methoxyresorcinol

2-bromo-5-methoxybenzene-1,3-diol