N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

Base Information

Chemical Name:N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide
CAS No.:267408-70-8
Molecular Formula:C₁₉H₂₆BrNO₃Si
Molecular Weight:424.41
Hs Code.:

Synonyms:N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

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Technology Process of N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

There total 5 articles about N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide 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: 85.0%

: 107-21-1
ethylene glycol

: 3-(tert-butyl-dimethyl-silanyl)-propynoic acid (2-bromo-phenyl)-(2-oxo-ethyl)-amide

: 267408-70-8
N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

Guidance literature:: With toluene-4-sulfonic acid; In toluene;
DOI:10.1039/a907920c

Reference yield:

: 615-36-1
2-bromoaniline

: 267408-70-8
N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / DCC / CH₂Cl₂ / 3.5 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

2.2: 68 percent / tetrahydrofuran / 1 h / 20 °C

3.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

3.2: 99 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

4.1: ozone / CH₂Cl₂; methanol / -78 - 20 °C

4.2: 62 percent / Me₂S / CH₂Cl₂; methanol / 16 h / 20 °C

5.1: 85 percent / p-TsOH / toluene

With sodium hydride; toluene-4-sulfonic acid; ozone; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Acylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Metallation / 3.2: Substitution / 4.1: Oxidation / 4.2: Reduction / 5.1: Cyclization;
DOI:10.1039/a907920c

Reference yield:

: 267408-59-3
N-(2'-Bromophenyl)propynamide

: 267408-70-8
N-(2'-Bromophenyl)-N-(1,3-dioxolan-2-ylmethyl)-3-tert-butyldimethylsilylpropynamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C

1.2: 68 percent / tetrahydrofuran / 1 h / 20 °C

2.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -78 °C

2.2: 99 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: ozone / CH₂Cl₂; methanol / -78 - 20 °C

3.2: 62 percent / Me₂S / CH₂Cl₂; methanol / 16 h / 20 °C

4.1: 85 percent / p-TsOH / toluene

With sodium hydride; toluene-4-sulfonic acid; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: Metallation / 2.2: Substitution / 3.1: Oxidation / 3.2: Reduction / 4.1: Cyclization;
DOI:10.1039/a907920c