ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate

Base Information

• Chemical Name: ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate
• CAS No.: 135145-45-8
• Molecular Formula: C₁₉H₂₂BrClO₄
• Molecular Weight: 429.738
• Mol file: 135145-45-8.mol

Synonyms:

Chemical Property of ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate

There total 7 articles about ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate 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:

(1R,4S,6S,7R)-4-[2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-propyl-phenoxy]-bicyclo[4.1.0]hept-2-ene-7-carboxylic acid ethyl ester (135145-44-7) → ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate (135145-45-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h;

DOI:10.1021/jo00018a015

Reference yield:

5-Methoxy-2-propyl-phenol (85696-74-8) → ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate (135145-45-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / SO₂Cl₂ / diethyl ether / 1.5 h

2: 92 percent / Br₂ / acetic acid / 0.75 h

3: 6.5 g / imidazole / dimethylformamide / 1.5 h

4: BBr₃ / CH₂Cl₂ / 1.5 h / 0 °C

5: 1.) diethyl azodicarboxylate, Ph₃P / 1.) THF a) 1 h, -30 deg C, b) 1 h, -20 deg C, 2.) THF, -20 deg C, 1 h

6: 1.19 g / Bu₄NF / tetrahydrofuran / 1.5 h

With 1H-imidazole; sulfuryl dichloride; tetrabutyl ammonium fluoride; bromine; boron tribromide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00018a015

Reference yield:

4-chloro-5-methoxy-2-propylbenzenol (135145-41-4) → ethyl (1α,3α,6α,7α)-(+/-)-3-(2-bromo-6-chloro-3-hydroxy-4-propylphenoxy)bicyclo<4.1.0>hept-4-ene-7-carboxylate (135145-45-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / Br₂ / acetic acid / 0.75 h

2: 6.5 g / imidazole / dimethylformamide / 1.5 h

3: BBr₃ / CH₂Cl₂ / 1.5 h / 0 °C

4: 1.) diethyl azodicarboxylate, Ph₃P / 1.) THF a) 1 h, -30 deg C, b) 1 h, -20 deg C, 2.) THF, -20 deg C, 1 h

5: 1.19 g / Bu₄NF / tetrahydrofuran / 1.5 h

With 1H-imidazole; tetrabutyl ammonium fluoride; bromine; boron tribromide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00018a015

upstream raw materials:

(1R,4S,6S,7R)-4-[2-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-propyl-phenoxy]-bicyclo[4.1.0]hept-2-ene-7-carboxylic acid ethyl ester

5-Methoxy-2-propyl-phenol

4-chloro-5-methoxy-2-propylbenzenol

2-bromo-4-chloro-3-methoxy-6-propylbenzenol