2-Naphthalenecarboxylic acid, 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxy-, 2-(trimethylsilyl)ethyl ester

Base Information

• Chemical Name: 2-Naphthalenecarboxylic acid, 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxy-, 2-(trimethylsilyl)ethyl ester
• CAS No.: 140110-69-6
• Molecular Formula: C27H33BrO6Si
• Molecular Weight: 561.545
• Mol file: 140110-69-6.mol

Synonyms:

Chemical Property of 2-Naphthalenecarboxylic acid, 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxy-, 2-(trimethylsilyl)ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Naphthalenecarboxylic acid, 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxy-, 2-(trimethylsilyl)ethyl ester

There total 6 articles about 2-Naphthalenecarboxylic acid, 3-(2-bromo-6-methoxy-4-methylphenyl)-1,4,8-trimethoxy-, 2-(trimethylsilyl)ethyl ester 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%

dimethylsulfite (616-42-2) + 2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate (133129-31-4) → 2-(trimethylsilyl)ethyl 1,4,8-trimethoxy-3-(2-bromo-6-methoxy-4-methylphenyl)naphthalene-2-carboxylate (140110-69-6)

Guidance literature:

With sodium dithionite; potassium carbonate; In acetone; for 24h; Heating;

DOI:10.1021/jo00007a009

Reference yield: 77.0%

2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate (133129-31-4) + dimethyl sulfate (77-78-1) → 2-(trimethylsilyl)ethyl 1,4,8-trimethoxy-3-(2-bromo-6-methoxy-4-methylphenyl)naphthalene-2-carboxylate (140110-69-6)

Guidance literature:

With sodium dithionite; potassium carbonate; In acetone; for 20h; Heating;

DOI:10.1021/jo00036a005

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 2-(trimethylsilyl)ethyl 1,4,8-trimethoxy-3-(2-bromo-6-methoxy-4-methylphenyl)naphthalene-2-carboxylate (140110-69-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / BuLi / tetrahydrofuran; hexane / 2 h / Heating

2: 93 percent / K₂CO₃ / acetone / 2 h / Heating

3: 1.) LDA, 2.) O₂ / 1a.) THF, hexane, -78, 1 h, 1b.) r. t., 48 h, 2.) 3 h

4: 77 percent / K₂CO₃, Na₂S₂O₄ / acetone / 20 h / Heating

With n-butyllithium; sodium dithionite; oxygen; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone;

DOI:10.1021/jo00036a005

upstream raw materials:

dimethylsulfite

2-(trimethylsilyl)ethyl 3-(2-bromo-6-methoxy-4-methylphenyl)-8-methoxy-1,4-naphthoquinone-2-carboxylate

dimethyl sulfate

2-(Trimethylsilyl)ethanol

Downstream raw materials:

1,4,8-trimethoxy-3-(2-methoxy-6-formyl-4-methylphenyl)naphthalene-2-carboxamide

1,4,8-trimethoxy-3-(2-methoxy-4-methylphenyl)naphthalene-2-carboxamide

methyl (1,4,8-trimethoxy-3-(5-bromo-2-methoxy-4-methylphenyl)naphthalen-2-yl)carbamate

1,4,8-trimethoxy-3-(2-bromo-4-methyl-6-methoxyphenyl)naphthalene-2-carboxamide