diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

Base Information

Chemical Name:diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate
CAS No.:943141-83-1
Molecular Formula:C₂₈H₃₄ClO₄P
Molecular Weight:501.002
Hs Code.:

Synonyms:diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

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Chemical Property of diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

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Technology Process of diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

There total 10 articles about diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate 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%

: 943141-82-0
diethyl (E)-2-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]ethenylphosphonate

: 943141-83-1
diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

Guidance literature:: With boron tribromide; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/jm0613323

Reference yield:

: 736992-49-7
2-(1-adamantyl)-1-benzyloxy-4-bromobenzene

: 943141-83-1
diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

1.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

2.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

3.1: 98 percent / aq. NaOH / CH₂Cl₂ / 0.17 h

4.1: 87 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; n-butyllithium; boron tribromide; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; 2.1: Suzuki-Miyaura coupling / 3.1: Horner-Emmons-Wadsworth olefination;
DOI:10.1021/jm0613323

Reference yield:

: 106-41-2
4-bromo-phenol

: 943141-83-1
diethyl (E)-2-[3'-(1-adamantyl)-2-chloro-4'-hydroxy-4-biphenyl]ethenylphosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: conc. sulfuric acid / CH₂Cl₂

2.1: K₂CO₃ / acetone / Heating

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

3.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

4.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

5.1: 98 percent / aq. NaOH / CH₂Cl₂ / 0.17 h

6.1: 87 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; n-butyllithium; boron tribromide; sodium carbonate; potassium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; 1.1: Friedel-Crafts alkylation / 4.1: Suzuki-Miyaura coupling / 5.1: Horner-Emmons-Wadsworth olefination;
DOI:10.1021/jm0613323