2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman

Base Information

• Chemical Name: 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman
• CAS No.: 1153673-84-7
• Molecular Formula: C₂₄H₂₃BrO₄
• Molecular Weight: 455.348
• Mol file: 1153673-84-7.mol

Synonyms:2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman

Chemical Property of 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman

There total 6 articles about 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman 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%

5-bromo-4-methoxy-2-methoxymethyloxybenzyl acetate (1153673-79-0) + 2-(3-benzyloxy-4-methoxyphenyl)ethylene (68360-39-4) → 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman (1153673-84-7)

Guidance literature:

With p-toluenesulfonic acid immobilized on silica; In toluene; at 0 - 20 ℃;

DOI:10.1021/jo900504y

Reference yield:

5-bromo-4-methoxy-2-methoxymethoxybenzaldehyde → 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman (1153673-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C

2: dmap; triethylamine / dichloromethane / 20 °C / Cooling with ice

3: p-toluenesulfonic acid on sillica gel / toluene / 0 - 20 °C

With dmap; sodium tetrahydroborate; p-toluenesulfonic acid on sillica gel; triethylamine; In ethanol; dichloromethane; toluene; 3: Diels-Alder reaction;

DOI:10.1016/j.tet.2011.03.059

Reference yield:

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) → 2-((3-benzyloxy-4-methoxy)phenyl)-6-bromo-7-methoxychroman (1153673-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bromine; acetic acid / 1 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

2.2: 2 h / 0 - 20 °C

3.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C

4.1: dmap; triethylamine / dichloromethane / 20 °C / Cooling with ice

5.1: p-toluenesulfonic acid on sillica gel / toluene / 0 - 20 °C

With dmap; sodium tetrahydroborate; p-toluenesulfonic acid on sillica gel; bromine; sodium hydride; acetic acid; triethylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 5.1: Diels-Alder reaction;

DOI:10.1016/j.tet.2011.03.059

upstream raw materials:

5-bromo-4-methoxy-2-methoxymethyloxybenzyl acetate

2-(3-benzyloxy-4-methoxyphenyl)ethylene

2-Hydroxy-4-methoxybenzaldehyde

5-bromo-4-methoxy-2-methoxymethyloxybenzyl alcohol

Refernces

• 1、 Batsomboon, Paratchata,Phakhodee, Wong,Ruchirawat, Somsak,Ploypradith, Poonsakdi. "Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes". experimental part. p. 4009 - 4012. Retrieved 2009/10/14.