Phenol, 5-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-3-(phenylmeth oxy)-, 1-(4-methylbenzenesulfonate)

Base Information

• Chemical Name: Phenol, 5-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-3-(phenylmeth oxy)-, 1-(4-methylbenzenesulfonate)
• CAS No.: 924888-05-1
• Molecular Formula: C27H33BrO5SSi
• Molecular Weight: 577.612
• Mol file: 924888-05-1.mol

Synonyms:

Chemical Property of Phenol, 5-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-3-(phenylmeth oxy)-, 1-(4-methylbenzenesulfonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenol, 5-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-3-(phenylmeth oxy)-, 1-(4-methylbenzenesulfonate)

There total 8 articles about Phenol, 5-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-3-(phenylmeth oxy)-, 1-(4-methylbenzenesulfonate) 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: 87.0%

toluene-4-sulfonic acid 3-benzyloxy-5-bromo-4-hydroxy-2-methyl-phenyl ester (919288-55-4) + tert-butyldimethylsilyl chloride (18162-48-6) → toluene-4-sulfonic acid 3-benzyloxy-5-bromo-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl ester (924888-05-1)

Guidance literature:

With TEA; for 0.75h;

DOI:10.1021/ja0670254

Reference yield:

toluene-4-sulfonic acid 3-benzyloxy-4-hydroxy-2-methyl-phenyl ester (919288-67-8) → toluene-4-sulfonic acid 3-benzyloxy-5-bromo-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl ester (924888-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / N-bromosuccinamide / CH₂Cl₂ / 0 °C

2: 87 percent / TEA / 0.75 h

With N-bromosuccinamide; TEA; In dichloromethane;

DOI:10.1021/ja0670254

Reference yield:

toluene-4-sulfonic acid 4-formyl-3-hydroxy-2-methyl-phenyl ester (924888-18-6) → toluene-4-sulfonic acid 3-benzyloxy-5-bromo-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl ester (924888-05-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / potassium carbonate; tetrabutylammonium iodide / acetone / 1.5 h / Heating

2: mCPBA / CH₂Cl₂ / 20 °C

3: 26.5 g / TEA; MeOH / CH₂Cl₂ / 0.67 h

4: 85 percent / N-bromosuccinamide / CH₂Cl₂ / 0 °C

5: 87 percent / TEA / 0.75 h

With methanol; N-bromosuccinamide; TEA; tetra-(n-butyl)ammonium iodide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone;

DOI:10.1021/ja0670254

upstream raw materials:

toluene-4-sulfonic acid 3-benzyloxy-5-bromo-4-hydroxy-2-methyl-phenyl ester

tert-butyldimethylsilyl chloride

toluene-4-sulfonic acid 3-benzyloxy-4-hydroxy-2-methyl-phenyl ester

toluene-4-sulfonic acid 4-formyl-3-hydroxy-2-methyl-phenyl ester

Downstream raw materials:

toluene-4-sulfonic acid 3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-[1-(2-hydroxy-ethyl)-vinyl]-2-methyl-phenyl ester

Refernces