(Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione

Base Information

• Chemical Name: (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione
• CAS No.: 310903-96-9
• Molecular Formula: C₁₄H₁₅BrN₂O₄
• Molecular Weight: 355.188
• Mol file: 310903-96-9.mol

Synonyms:(Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione

Chemical Property of (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione

There total 5 articles about (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione 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: 85.2%

(Z)-3-(2-bromo-5-isopropoxy-4-methoxy-3-methylphenylmethylene)-4-(4-methoxyphenylmethyl)-1-methyl-2,5-piperazinedione (310903-95-8) → (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione (310903-96-9)

Guidance literature:

With sulfuric acid; trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1248/cpb.48.1549

Reference yield:

2-bromo-5-isopropyloxy-4-methoxy-3-methylbenzaldehyde (287117-38-8) → (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione (310903-96-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 74.3 percent / KOtBu / 2-methyl-propan-2-ol; dimethylformamide / 1 h / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: dimethylformamide / 42 h / 20 °C

3.1: NH₂NH₂*H₂O / dimethylformamide / 1 h / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 78.6 percent / dimethylformamide / 3 h / 20 °C

5.1: 85.2 percent / TFA; H₂SO₄ / 1 h / 20 °C

With sulfuric acid; potassium tert-butylate; sodium hydride; hydrazine hydrate; trifluoroacetic acid; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1248/cpb.48.1549

Reference yield:

(Z)-1-acetyl-3-(2-bromo-5-isopropoxy-4-methoxy-3-methylphenylmethylene)-2,5-piperazinedione (310903-92-5) → (Z)-3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethylene)-1-methyl-2,5-piperazinedione (310903-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: dimethylformamide / 42 h / 20 °C

2.1: NH₂NH₂*H₂O / dimethylformamide / 1 h / 20 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 78.6 percent / dimethylformamide / 3 h / 20 °C

4.1: 85.2 percent / TFA; H₂SO₄ / 1 h / 20 °C

With sulfuric acid; sodium hydride; hydrazine hydrate; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1549

upstream raw materials:

(Z)-3-(2-bromo-5-isopropoxy-4-methoxy-3-methylphenylmethylene)-4-(4-methoxyphenylmethyl)-1-methyl-2,5-piperazinedione

2-bromo-5-isopropyloxy-4-methoxy-3-methylbenzaldehyde

(Z)-1-acetyl-3-(2-bromo-5-isopropoxy-4-methoxy-3-methylphenylmethylene)-2,5-piperazinedione

(Z)-3-(2-bromo-5-isopropoxy-4-methoxy-3-methylphenylmethylene)-4-(4-methoxyphenylmethyl)-2,5-piperazinedione

Downstream raw materials:

3-(2-bromo-5-hydroxy-4-methoxy-3-methyl-6-phenylmethyl-phenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione

3-(5-benzyloxy-2-bromo-4-methoxy-3-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione

2-(5-benzyloxy-2-bromo-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione