[6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile

Base Information

• Chemical Name: [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile
• CAS No.: 482374-41-4
• Molecular Formula: C₁₆H₁₆BrNO₃
• Molecular Weight: 350.212
• Mol file: 482374-41-4.mol

Synonyms:[6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile

Chemical Property of [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile

There total 14 articles about [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile 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: 71.0%

(-)-2-bromo-3-(2-hydroxymethylcyclohex-2-enyloxy)-4-methoxybenzaldehyde + sodium cyanide (773837-37-9) → [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile (482374-41-4)

Guidance literature:

(-)-2-bromo-3-(2-hydroxymethylcyclohex-2-enyloxy)-4-methoxybenzaldehyde; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

sodium cyanide; In dimethyl sulfoxide; at 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jo400355j

Reference yield:

2-hydroxy-2-methylpropanenitrile (75-86-5) + [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol (482374-40-3) → [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile (482374-41-4)

Guidance literature:

[6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol; With di-isopropyl azodicarboxylate; triphenylphosphine; In diethyl ether; at -20 ℃; for 0.333333h;

2-hydroxy-2-methylpropanenitrile; In diethyl ether; at -20 - 20 ℃; for 12h;

With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja054449+

Reference yield:

[(S)-6-(2-Bromo-3-dimethoxymethyl-6-methoxy-phenoxy)-cyclohex-1-enyl]-acetonitrile (869369-38-0) → [6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]acetonitrile (482374-41-4)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1002/1521-3773(20020802)41:15<2795::AID-ANIE2795>3.0.CO;2-2

upstream raw materials:

[(S)-6-(2-Bromo-3-dimethoxymethyl-6-methoxy-phenoxy)-cyclohex-1-enyl]-acetonitrile

2-hydroxy-2-methylpropanenitrile

[6-(2-bromo-3-dimethoxymethyl-6-methoxyphenoxy)cyclohex-1-enyl]methanol

methyl 6-hydroxy-cyclohex-1-enecarboxylate

Downstream raw materials:

Galantamine

(-)-epigalanthamine

codeine

MORPHIN

Refernces

• 1、 Trost, Barry M.,Tang, Weiping,Toste, F. Dean. "Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine". . p. 14785 - 14803. Retrieved 2007/10/03.