1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

Base Information

• Chemical Name: 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline
• CAS No.: 87201-31-8
• Molecular Formula: C₁₇H₁₄BrNO₂
• Molecular Weight: 344.208
• Mol file: 87201-31-8.mol

Synonyms:1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

Chemical Property of 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

There total 8 articles about 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline 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: 92.0%

N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide (87201-30-7) → 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (87201-31-8)

Guidance literature:

With trichlorophosphate; In acetonitrile; for 3h; Heating;

DOI:10.1071/CH9831061

Reference yield:

2-(2-bromophenyl)acetonitrile (19472-74-3) + 3,4-methylenedioxyphenethyl alcohol (6006-82-2) → 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (87201-31-8)

Guidance literature:

With dmap; trifluoromethylsulfonic anhydride; In 1,2-dichloro-ethane; at 0 - 80 ℃; for 14.5h;

DOI:10.1016/j.tetlet.2020.152599

Reference yield:

ortho-bromophenylacetic acid (18698-97-0) → 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline (87201-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl₂); dimethylformamide / CH₂Cl₂ / 25 °C

2: Et₃N / CH₂Cl₂ / 25 °C

3: POCl₃ / CH₂Cl₂ / 12 h / Heating

With phosgene; triethylamine; N,N-dimethyl-formamide; trichlorophosphate; In dichloromethane; 3: Bischler-Napieralski cyclization;

DOI:10.1002/ejoc.200600674

upstream raw materials:

N-<-2-(3,4-methylenedioxyphenyl)ethyl>-2'-bromophenylacetamide

ortho-bromophenylacetic acid

2-bromophenylacetyl chloride

2-bromo-ω-diazoacetophenone

Downstream raw materials:

ethyl (Z)-1-(2-bromobenzylidene)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

(2-bromophenyl)(7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone

5-(2-bromobenzyl)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline

(+)-roemerine