2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione
• CAS No.: 944263-04-1
• Molecular Formula: C₂₂H₂₆INO₃Si
• Molecular Weight: 507.443
• Mol file: 944263-04-1.mol

Synonyms:2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione

Chemical Property of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione

There total 4 articles about 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione 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:

phthalic anhydride (85-44-9) + 5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenylamine (389091-74-1) → 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione (944263-04-1)

Guidance literature:

With triethylamine; In toluene; Heating;

DOI:10.1021/ol0168871

Reference yield:

3-(hydroxymethyl)-6-methylaniline (81863-45-8) → 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione (944263-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: benzyltrimethylammonium dichloroiodate; CaCO₃ / CH₂Cl₂; methanol / 0.5 h / 20 °C

2: triethylamine / toluene / 3.5 h / Heating

With N,N,N-trimethylbenzenemethanaminium dichloroiodate; triethylamine; calcium carbonate; In methanol; dichloromethane; toluene;

DOI:10.1021/jo062422i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione (944263-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide

2: 99 percent / BTMA*ICl₂; Caco₃ / methanol; CH₂Cl₂

3: Et₃N / toluene / Heating

With 1H-imidazole; N,N,N-trimethylbenzenemethanaminium dichloroiodate; triethylamine; calcium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol0168871

upstream raw materials:

phthalic anhydride

5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenylamine

3-(hydroxymethyl)-6-methylaniline

tert-butyldimethylsilyl chloride

Downstream raw materials:

2-(5-hydroxymethyl-4-iodo-2-methyl-phenyl)-isoindole-1,3-dione

2-(5-bromomethyl-4-iodo-2-methyl-phenyl)-isoindole-1,3-dione

2-[4-Iodo-2-methyl-5-((R)-2,2,6,6-tetramethyl-4-oxo-tetrahydro-pyran-3-ylmethyl)-phenyl]-isoindole-1,3-dione

trifluoro-methanesulfonic acid 3-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-iodo-4-methyl-benzyl]-2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl ester