3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate

Base Information

• Chemical Name: 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate
• CAS No.: 1369625-86-4
• Molecular Formula: C₂₁H₂₉BrN₂O₂Si
• Molecular Weight: 449.463
• Mol file: 1369625-86-4.mol

Synonyms:3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate

Chemical Property of 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate

There total 4 articles about 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate 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: 79.0%

2-[(2-bromophenyl)(diisopropyl)silyl]pyrimidine (1369625-72-8) + bis(tertbutylcarbonyloxy)iodobenzene (57357-20-7) → 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate (1369625-86-4)

Guidance literature:

With lithium acetate; palladium diacetate; In 1,2-dichloro-ethane; at 80 ℃; for 22h; Concentration; Time; Inert atmosphere; Glovebox; Schlenk technique;

DOI:10.1002/anie.201304884

Reference yield:

2-(diisopropyl(phenyl)silyl)pyrimidine (1369625-51-3) → 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate (1369625-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; palladium diacetate / 1,2-dichloro-ethane / 60 °C / Inert atmosphere

2: lithium acetate; palladium diacetate / 1,2-dichloro-ethane / 20 h / 80 °C / Inert atmosphere

With N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; lithium acetate; palladium diacetate; In 1,2-dichloro-ethane;

DOI:10.1021/ja3010545

Reference yield:

2-(diisopropylsilyl)pyrimidine (1369625-74-0) → 3-bromo-2-[diisopropyl(pyrimidin-2-yl)silyl]phenyl pivalate (1369625-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium phosphate; dirhodium tetraacetate / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere

2: N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; palladium diacetate / 1,2-dichloro-ethane / 60 °C / Inert atmosphere

3: lithium acetate; palladium diacetate / 1,2-dichloro-ethane / 20 h / 80 °C / Inert atmosphere

With dirhodium tetraacetate; potassium phosphate; N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; lithium acetate; palladium diacetate; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1021/ja3010545

upstream raw materials:

2-(diisopropylsilyl)pyrimidine

2-(diisopropyl(phenyl)silyl)pyrimidine

2-[(2-bromophenyl)(diisopropyl)silyl]pyrimidine

bis(tertbutylcarbonyloxy)iodobenzene

Downstream raw materials:

3-Bromophenol

Refernces

• 1、 Gulevich, Anton V.,Melkonyan, Ferdinand S.,Sarkar, Dhruba,Gevorgyan, Vladimir. "Double-fold C-H oxygenation of arenes using PyrDipSi: A general and efficient traceless/modifiable silicon-tethered directing group". . p. 5528 - 5531. Retrieved 2012/05/20.