Ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Base Information

• Chemical Name: Ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate
• CAS No.: 179420-76-9
• Molecular Formula: C₁₄H₁₇BrO₃
• Molecular Weight: 313.191
• DSSTox Substance ID: DTXSID801236436
• Nikkaji Number: J2.201.729B
• Mol file: 179420-76-9.mol

Synonyms:SCHEMBL7807438;GVKOGJQHZDQALH-UHFFFAOYSA-N;DTXSID801236436;179420-76-9;ethyl 4-(3-bromophenyl)tetrahydro-2H-pyran-4-carboxylate;Ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Chemical Property of Ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 312.03611
• Heavy Atom Count: 18
• Complexity: 287

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CCOCC1)C2=CC(=CC=C2)Br

Technology Process of Ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

There total 2 articles about Ethyl 4-(3-bromophenyl)-3,4,5,6-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: 69.0%

silica-gel + ethyl acetate-toluene + ethyl 2-(3-bromophenyl)acetate (14062-30-7) + 3-oxa-1,5-dichloropentane (111-44-4) → ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-76-9)

Guidance literature:

With sodium iodide; In hexane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield: 69.0%

ethyl 2-(3-bromophenyl)acetate (14062-30-7) + 3-oxa-1,5-dichloropentane (111-44-4) → ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-76-9)

Guidance literature:

ethyl 2-(3-bromophenyl)acetate; With 15-crown-5; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.666667h;

3-oxa-1,5-dichloropentane; With sodium iodide; In N,N-dimethyl-formamide; for 10.5h;

DOI:10.1248/cpb.53.965

Reference yield:

ethyl 4-(3-bromophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-76-9) → methyl 4-(3-mercaptophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (179420-81-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / aq. LiOH / methanol; tetrahydrofuran / 24 h / Heating

2.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 - -70 °C

2.2: 21.5 g / hexane; tetrahydrofuran / 4.17 h / -78 - 20 °C

3.1: 17.9 g / HCl / 20 h / Heating

4.1: 12.2 g / aq. sodium periodate / methanol / 1 h / 0 °C

5.1: trifluoroacetic anhydride / 0.5 h / Heating

5.2: Et₃N; MeOH

With hydrogenchloride; lithium hydroxide; sodium periodate; n-butyllithium; trifluoroacetic anhydride; In tetrahydrofuran; methanol; hexane;

DOI:10.1248/cpb.53.965

upstream raw materials:

ethyl 2-(3-bromophenyl)acetate

3-oxa-1,5-dichloropentane

Downstream raw materials:

methyl 4-(3-mercaptophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

4-(3-methylsulfanyl-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester

4-(3-methylsulfanyl-phenyl)-tetrahydro-pyran-4-carboxylic acid

methyl 4-(3-methylsulfinylphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate