ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate

Base Information

• Chemical Name: ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate
• CAS No.: 134276-55-4
• Molecular Formula: C₁₆H₂₁Br₂NO₃
• Molecular Weight: 435.156
• Mol file: 134276-55-4.mol

Synonyms:ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate

Chemical Property of ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate

There total 3 articles about ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate 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: 78.0%

hydrogen ethyl malonate (1071-46-1) + 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)benzaldehyde (134276-57-6) → ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate (134276-55-4)

Guidance literature:

With pyridine; piperidine; 1) overnight, 2) 60 deg C, 6 h;

DOI:10.1016/S0040-4020(01)96095-8

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate (134276-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / n-butylamine, Br₂ / toluene; CH₂Cl₂; methanol / -78 °C

2: 1) NaH / 1) THF, 2) toluene, THF, reflux, 2.5 h

3: 78 percent / pyridine / piperidine / 1) overnight, 2) 60 deg C, 6 h

With pyridine; bromine; sodium hydride; N-butylamine; piperidine; In methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)96095-8

Reference yield:

3,5-dibromo-4-hydroxybenzaldehyde (2973-77-5) → ethyl 3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)cinnamate (134276-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH / 1) THF, 2) toluene, THF, reflux, 2.5 h

2: 78 percent / pyridine / piperidine / 1) overnight, 2) 60 deg C, 6 h

With pyridine; sodium hydride; piperidine;

DOI:10.1016/S0040-4020(01)96095-8

upstream raw materials:

hydrogen ethyl malonate

3,5-dibromo-4-(3'-N,N-dimethylaminopropyloxy)benzaldehyde

3,5-dibromo-4-hydroxybenzaldehyde

4-hydroxy-benzaldehyde

Downstream raw materials:

(E)-3-[3,5-dibromo-4-(3-dimethylaminopropoxy)phenyl]acrylic acid