methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate

Base Information

• Chemical Name: methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate
• CAS No.: 343256-46-2
• Molecular Formula: C₁₃H₁₅Br₂NO₆
• Molecular Weight: 441.073
• Mol file: 343256-46-2.mol

Synonyms:methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate

Chemical Property of methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate

There total 4 articles about methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate 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: 90.0%

methyl 2-{(1,1-dimethylethyl)dimethylsilyloxy}-3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}prop-2-enoate (343256-44-0) → methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate (343256-46-2)

Guidance literature:

methyl 2-{(1,1-dimethylethyl)dimethylsilyloxy}-3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}prop-2-enoate; With triethylamine hydrofluoride; In methanol;

With hydroxylamine hydrochloride; In methanol; Further stages.;

DOI:10.1021/jo010015v

Reference yield:

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) → methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate (343256-46-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / NBS / dimethylformamide / 0.25 h / 0 °C

2.1: 99 percent / iPr₂NEt / tetrahydrofuran / 0 - 20 °C

3.1: 92 percent / iPr₂NH; n-BuLi / tetrahydrofuran / -78 °C

4.1: Et₃N*HF / methanol

4.2: 90 percent / NH₂OH*HCl / methanol

With N-Bromosuccinimide; n-butyllithium; triethylamine hydrofluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3.1: Wadsworth-Emmons olefination;

DOI:10.1021/jo010015v

Reference yield:

3,5-dibromo-2-hydroxy-4-methoxy benzaldehyde (117238-61-6) → methyl 3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}2(E)-(hydroxyimino)propanoate (343256-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / iPr₂NEt / tetrahydrofuran / 0 - 20 °C

2.1: 92 percent / iPr₂NH; n-BuLi / tetrahydrofuran / -78 °C

3.1: Et₃N*HF / methanol

3.2: 90 percent / NH₂OH*HCl / methanol

With n-butyllithium; triethylamine hydrofluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 2.1: Wadsworth-Emmons olefination;

DOI:10.1021/jo010015v

upstream raw materials:

methyl 2-{(1,1-dimethylethyl)dimethylsilyloxy}-3-{3,5-dibromo-4-methoxy-2-(O-methoxymethylenoxy)phenyl}prop-2-enoate

2-Hydroxy-4-methoxybenzaldehyde

3,5-dibromo-2-hydroxy-4-methoxy benzaldehyde

3,5-dibromo-2-(O-methoxymethylenoxy)-4-methoxybenzaldehyde

Downstream raw materials:

3,5-dibromo-2-hydroxy-4-methoxyphenylacetonitrile

3,5-dibromo-4-methoxy-2(methoxymethylenoxy)benzylnitrile

3-(3,5-dibromo-4-methoxy-2-methoxymethoxy-phenyl)-2-hydroxyimino-N-[2-(3H-imidazol-4-yl)-ethyl]-propionamide

methyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanoate