trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone

Base Information

• Chemical Name: trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone
• CAS No.: 137718-83-3
• Molecular Formula: C₁₂H₂₃BrO₂Si
• Molecular Weight: 307.303
• Mol file: 137718-83-3.mol

Synonyms:trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone

Chemical Property of trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone

There total 4 articles about trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone 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:

tert-butyl-(4-methoxycyclohex-3-enyloxy)dimethylsilane (137718-78-6) → trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone (137718-83-3) + cis-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone (137718-79-7)

Guidance literature:

With N-Bromosuccinimide; sodium acetate; In tetrahydrofuran; water; at 0 ℃; for 4h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00028a066

Reference yield:

4-hydroxy-1-methoxy-1-cyclohexene (69125-55-9) → trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone (137718-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

2: 1.) NBS, NaOAc, 2.) SiO₂ / 1.) THF, H₂O, 0 deg C, 4 h

With 1H-imidazole; N-Bromosuccinimide; sodium acetate; silica gel; In N,N-dimethyl-formamide;

DOI:10.1021/jo00028a066

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → trans-2-bromo-4-(tert-butyldimethylsiloxy)cyclohexanone (137718-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

2: 1.) NBS, NaOAc, 2.) SiO₂ / 1.) THF, H₂O, 0 deg C, 4 h

With 1H-imidazole; N-Bromosuccinimide; sodium acetate; silica gel; In N,N-dimethyl-formamide;

DOI:10.1021/jo00028a066

upstream raw materials:

tert-butyl-(4-methoxycyclohex-3-enyloxy)dimethylsilane

4-hydroxy-1-methoxy-1-cyclohexene

tert-butyldimethylsilyl chloride

Downstream raw materials:

[(2R,4R)-2-{2-Bromo-3-[(tert-butoxycarbonyl-methyl-amino)-methyl]-6-methoxy-phenoxy}-4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-(E)-ylidene]-acetic acid methyl ester

(+/-)-trans-3,5-bis(t-butyldimethylsiloxy)-2-methylenecyclohexanone