4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane

Base Information

• Chemical Name: 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane
• CAS No.: 185244-55-7
• Molecular Formula: C₁₃H₁₅BrO₂
• Molecular Weight: 283.165
• Mol file: 185244-55-7.mol

Synonyms:4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane

Chemical Property of 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane

There total 1 articles about 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane 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:

5-bromo-2-methoxyphenol (37942-01-1) → 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane (185244-55-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 69 percent / K₂CO₃ / dimethylformamide / 2.5 h / 60 °C

2.1: KOtBu / tetrahydrofuran / 2 h

2.2: tetrahydrofuran / 1 h

3.1: 20.3 g / 0.75 h / 180 °C

4.1: 95 percent / Amberlyst 15 ion-exchange resin / toluene / 3 h / 80 °C

With Amberlyst 15 ion-exchange resin; potassium tert-butylate; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 2.1: Wittig reaction / 3.1: Claisen rearrangement;

DOI:10.1021/jm010838c

Reference yield: 70.0%

1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) + 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane (185244-55-7) → cis-(+/-)-2-(2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane-4-carbonyl)cyclohexanecarboxylic acid

Guidance literature:

4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane; With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 0.25h;

1,2-cis-cyclohexanedicarboxylic anhydride; In tetrahydrofuran; hexane; at -80 ℃; for 2h; Further stages.;

DOI:10.1021/jm010838c

Reference yield: 52.0%

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) + 4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane (185244-55-7) → cis-(+/-)-2-(2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane-4-carbonyl)-1,2,3,6-tetrahydrobenzoic acid

Guidance literature:

4-bromo-2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentane; With magnesium; In tetrahydrofuran; for 22h;

cis-1,2,3,6-tetrahydrophthalic anhydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Further stages.;

DOI:10.1021/jm010838c

upstream raw materials:

5-bromo-2-methoxyphenol

Refernces