methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate

Base Information

• Chemical Name: methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate
• CAS No.: 1202765-53-4
• Molecular Formula: C₁₃H₁₄BrNO₅
• Molecular Weight: 344.162
• Mol file: 1202765-53-4.mol

Synonyms:methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate

Chemical Property of methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate

There total 2 articles about methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-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: 36.0%

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 4-bromo-2-nitro-benzoic acid methyl ester (100487-82-9) → methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (1202765-53-4)

Guidance literature:

4-bromo-2-nitro-benzoic acid methyl ester; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

1,1'-oxybis(2-bromo-ethane); With sodium iodide; In dimethyl sulfoxide; mineral oil; at 40 ℃; for 19h; Inert atmosphere;

DOI:10.1021/jm300679u

Reference yield:

4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (1202765-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Cooling with ice

1.2: Cooling with ice

2.1: water; lithium chloride / dimethyl sulfoxide / 20 - 100 °C

3.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 20 °C

3.2: 19 h / 40 °C

With water; sodium hydride; potassium carbonate; lithium chloride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield: 72.0%

methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (1202765-53-4) → 6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-2-one (1190861-43-8)

Guidance literature:

With iron; In acetic acid; at 100 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm300679u

upstream raw materials:

1,1'-oxybis(2-bromo-ethane)

4-bromo-2-nitro-benzoic acid methyl ester

4-Bromo-1-fluoro-2-nitrobenzene

Downstream raw materials:

6-bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-2-one

6-bromo-2',3',5',6'-tetrahydrospiro[dihydroindole-3,4'-pyran]

1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]