(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

Base Information

Chemical Name:(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran
CAS No.:473240-72-1
Molecular Formula:C₂₆H₂₃BrO₅
Molecular Weight:495.37
Hs Code.:

Synonyms:(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

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Chemical Property of (E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

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Technology Process of (E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

There total 5 articles about (E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran 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%

: 473240-70-9
(E)-3-[2-(4-Benzyloxy-3-methoxy-phenyl)-3-bromo-7-methoxy-benzofuran-5-yl]-acrylic acid ethyl ester

: 473240-72-1
(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 21h;
DOI:10.1021/jo0258960

Reference yield:

: 332077-62-0
1-(4-benzyloxy-3-methoxyphenyl)-2-(5-(5,5-dimethyl-1,3-dioxan-2-yl)-2,3-dimethoxyphenyl)acetylene

: 473240-72-1
(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

Guidance literature:: Multi-step reaction with 3 steps

1.1: bromine / CHCl₃ / 2 h / -15 °C

1.2: 86 percent / 6N hydrochloric acid / acetone / 3 h / 20 °C

2.1: 88 percent / tetrahydrofuran / 2 h / -78 °C

3.1: 73 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 21 h / 20 °C

With bromine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; chloroform; 2.1: Wittig reaction;
DOI:10.1021/jo0258960

Reference yield:

: 332077-60-8
1-(p-benzyloxy-m-methoxyphenyl)-1-(2,3-dimethoxy)-5-(5',5'-dimethyl-1',3'-dioxan-2'-yl)phenyl carbinol

: 473240-72-1
(E)-2-(4-benzyloxy-3-methoxyphenyl)-3-bromo-5-(3-hydroxyprop-1-en-1-yl)-7-methoxybenzofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / 90percent active MnO₂ / CH₂Cl₂ / 15 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.2: 98 percent / tetrahydrofuran / 5 h / -78 °C

3.1: bromine / CHCl₃ / 2 h / -15 °C

3.2: 86 percent / 6N hydrochloric acid / acetone / 3 h / 20 °C

4.1: 88 percent / tetrahydrofuran / 2 h / -78 °C

5.1: 73 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 21 h / 20 °C

With n-butyllithium; bromine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; chloroform; 2.2: Colvin rearrangement / 4.1: Wittig reaction;
DOI:10.1021/jo0258960