1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene

Base Information

• Chemical Name: 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene
• CAS No.: 181026-82-4
• Molecular Formula: C₁₄H₂₃BrO₂Si₂
• Molecular Weight: 359.41
• Mol file: 181026-82-4.mol

Synonyms:1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene

Chemical Property of 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene

There total 1 articles about 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene 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:

chloro-trimethyl-silane (75-77-4) + 2-bromophenylacetic acid (4870-65-9,31302-84-8) → 1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene (181026-82-4)

Guidance literature:

With lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to RT, 5 h;

Reference yield:

1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene (181026-82-4) → (R)-2-bromo-2-phenylacetic acid (60686-79-5,31302-84-8) + (+)-(S)-α-bromophenylacetic acid (60686-78-4,31302-84-8)

Guidance literature:

1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene; With (R)-BINOL-SnCl₄; In dichloromethane; toluene; at -78 ℃; for 1h;

With hydrogenchloride; In dichloromethane; toluene; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja001164i

Reference yield:

1,1-bis(trimethylsilyloxy)-2-bromo-2-phenylethene (181026-82-4) → (S)-(+)-methyl 2-bromo-2-phenylacetate (3042-81-7,61139-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (R)-BINOL-SnCl₄ / toluene; CH₂Cl₂ / 1 h / -78 °C

1.2: aq. HCl / toluene; CH₂Cl₂

With (R)-BINOL-SnCl₄; In dichloromethane; toluene; 1.1: enantioselective protonation / 1.2: Hydrolysis / 2.1: Esterification;

DOI:10.1021/ja001164i

upstream raw materials:

chloro-trimethyl-silane

2-bromophenylacetic acid

Downstream raw materials:

(S)-(+)-methyl 2-bromo-2-phenylacetate

methyl (α-bromo)phenylacetate

(R)-2-bromo-2-phenylacetic acid

(+)-(S)-α-bromophenylacetic acid