(E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile

Base Information

• Chemical Name: (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile
• CAS No.: 943141-56-8
• Molecular Formula: C₂₅H₂₄ClNO
• Molecular Weight: 389.925
• Mol file: 943141-56-8.mol

Synonyms:(E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile

Chemical Property of (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile

There total 11 articles about (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile 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%

(E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamonitrile (943141-55-7) → (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile (943141-56-8)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jm0613323

Reference yield:

(E)-3-chloro-4-hydroxycinnamonitrile (943141-53-5) → (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile (943141-56-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / CH₂Cl₂ / 20 °C

2: 69 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

3: 87 percent / BBr₃ / CH₂Cl₂ / 2 h / -78 °C

With pyridine; boron tribromide; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; dichloromethane; 2: Suzuki-Miyaura coupling;

DOI:10.1021/jm0613323

Reference yield:

(E)-3-(3-chloro-4-trifluoromethanesulfonyloxy)cinnamonitrile (943141-54-6) → (E)-4-[3'-(1-adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamonitrile (943141-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

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

With boron tribromide; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; dichloromethane; 1: Suzuki-Miyaura coupling;

DOI:10.1021/jm0613323

upstream raw materials:

(E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamonitrile

(E)-4-benzyloxy-3-chlorocinnamonitrile

(E)-3-chloro-4-hydroxycinnamonitrile

(E)-3-(3-chloro-4-trifluoromethanesulfonyloxy)cinnamonitrile

Refernces