3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone

Base Information

• Chemical Name: 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone
• CAS No.: 155722-63-7
• Molecular Formula: C₂₀H₁₉BrO₆
• Molecular Weight: 435.271
• Mol file: 155722-63-7.mol

Synonyms:3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone

Chemical Property of 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone

There total 9 articles about 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone 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:

2,6-Dibromo-4-methylaniline (6968-24-7) → 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone (155722-63-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 °C

2: 95 percent / sulfuric acid / 0.08 h

3: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl₂(PPh₃)2 / 18 h / 110 °C / 7600 Torr

4: 95 percent / 10percent NaOH / 1 h / Heating

5: 80 percent / HCl / 4 h

6: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min

With hydrogenchloride; sodium hydroxide; copper(l) iodide; tributyl-amine; sulfuric acid; water; triphenylphosphine; sodium nitrite; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86970-2

Reference yield:

p-toluidine (106-49-0,12221-03-3) → 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone (155722-63-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / bromine-dioxane complex / dioxane

2: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 °C

3: 95 percent / sulfuric acid / 0.08 h

4: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl₂(PPh₃)2 / 18 h / 110 °C / 7600 Torr

5: 95 percent / 10percent NaOH / 1 h / Heating

6: 80 percent / HCl / 4 h

7: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min

With hydrogenchloride; sodium hydroxide; copper(l) iodide; tributyl-amine; sulfuric acid; water; bromine; triphenylphosphine; sodium nitrite; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86970-2

Reference yield:

7-bromo-5,8-dimethoxy-1-tetralone (77199-82-7) → 3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyl-5,6,7,8-tetrahydrojuglone (155722-63-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaBH₄ / methanol / 3 h / Heating

2: 78 percent / ceric ammonium nitrate / H₂O; acetonitrile / 3-4 h

3: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min

With hydrogenchloride; sodium tetrahydroborate; ammonium cerium(IV) nitrate; sodium nitrite; In methanol; water; acetonitrile;

DOI:10.1016/S0040-4020(01)86970-2

upstream raw materials:

methyl-3-methoxy-5-methyl anthranilate

3-bromo-5,6,7,8-tetrahydrojuglone

2,6-Dibromo-4-methylaniline

7-bromo-5,8-dimethoxy-1-tetralone

Downstream raw materials:

3-bromo-2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone

Refernces