4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane

Base Information

• Chemical Name: 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane
• CAS No.: 79452-83-8
• Molecular Formula: C₁₁H₁₆BNO₃
• Molecular Weight: 221.064
• Mol file: 79452-83-8.mol

Synonyms:4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane

Chemical Property of 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane

There total 2 articles about 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane 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: 77.0%

1-bromo-4-methoxy-benzene (104-92-7) + 2,2'-iminobis[ethanol] (111-42-2) → 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane (79452-83-8)

Guidance literature:

1-bromo-4-methoxy-benzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

2,2'-iminobis[ethanol]; In diethyl ether; isopropyl alcohol;

DOI:10.1016/j.tetlet.2011.01.012

Reference yield: 77.0%

1-bromo-4-methoxy-benzene (104-92-7) + Triisopropyl borate (5419-55-6) + 2,2'-iminobis[ethanol] (111-42-2) → 4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane (79452-83-8)

Guidance literature:

With n-BuLi; NH₄Cl; In propan-2-ol; Br compd. treated with n-BuLi; triisopropylborate added; org. phase washed with satd. NH4Cl; treated with 3 M diethanolamine in iPrOH; filtered; crystd.;

DOI:10.1039/b926547n

Reference yield: 100.0%

4,5,7,8-tetrahydro-2-(4'-methoxyphenyl)-6H-[1,3,6,2]dioxazaborocane (79452-83-8) + para-bromoacetophenone (99-90-1) → 1-(4'-methoxy-biphenyl-4-yl)-ethanone (13021-18-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; copper(l) iodide; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.01.012

upstream raw materials:

1-bromo-4-methoxy-benzene

Triisopropyl borate

2,2'-iminobis[ethanol]

Downstream raw materials:

4-methoxy-4'-nitrobiphenyl

4,4'-Dimethoxybiphenyl

4-bromo-4'-methoxylbiphenyl

2-bromo-4'-methoxy-1,1'-biphenyl

Refernces

• 1、 Bonin, Helene,Delbrayelle, Dominique,Demonchaux, Patrice,Gras, Emmanuel. "Base free aryl coupling of diazonium compounds and boronic esters: Self-activation allowing an overall highly practical process". . p. 2677 - 2679. Retrieved 2010/07/08.