(E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene

Base Information

• Chemical Name: (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene
• CAS No.: 1566470-05-0
• Molecular Formula: C₁₅H₁₀ClF₃
• Molecular Weight: 282.693
• Mol file: 1566470-05-0.mol

Synonyms:(E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene

Chemical Property of (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene

There total 4 articles about (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene 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%

(Z)-1-phenyl-3,3,3-trifluoroprop-1-en-2-yl trifluoromethanesulfonate + tributyl(4-chlorophenyl)stannane (17151-48-3) → (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene (1566470-05-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; lithium chloride; In toluene; at 100 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.6b00855

Reference yield:

4'-chloro-2,2,2-trifluoroacetophenone (321-37-9) + benzaldehyde p-toluenesulfonylhydrazone (1666-17-7) → (Z)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene + (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene (1566470-05-0)

Guidance literature:

With copper(l) iodide; triphenylphosphine; lithium tert-butoxide; In toluene; at 90 ℃; for 10h; Overall yield = 75 %; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/cctc.201300583

Reference yield:

1-(4-chlorophenyl)-2,2,2-trifluoroethanol (72487-06-0,80418-11-7,446-66-2) → (E)-1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene (1566470-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) chloride; 1,10-Phenanthroline; diethyl hydrazodicarboxylate; oxygen; potassium carbonate / toluene / 90 °C

2: copper(l) iodide; triphenylphosphine; lithium tert-butoxide / toluene / 10 h / 90 °C / Inert atmosphere

With copper(l) iodide; 1,10-Phenanthroline; diethyl hydrazodicarboxylate; oxygen; potassium carbonate; triphenylphosphine; copper(l) chloride; lithium tert-butoxide; In toluene; 2: |Wittig Olefination;

DOI:10.1055/s-0034-1378231

upstream raw materials:

4'-chloro-2,2,2-trifluoroacetophenone

benzaldehyde p-toluenesulfonylhydrazone

1-(4-chlorophenyl)-2,2,2-trifluoroethanol

tributyl(4-chlorophenyl)stannane

Refernces

• 1、 Sha, Qiang,Wei, Yunyang. "Copper(i)-catalyzed wittig olefination reactions of N-tosylhydrazones with trifluoromethylketones". . p. 131 - 134. Retrieved 2014/01/23.