2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone

Base Information

• Chemical Name: 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone
• CAS No.: 866102-07-0
• Molecular Formula: C₁₂H₁₃BrO₂
• Molecular Weight: 269.138
• Mol file: 866102-07-0.mol

Synonyms:2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone

Chemical Property of 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone

There total 3 articles about 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone 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: 48.0%

3-(3-bromo-furan-2-ylmethyl)-2-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester (866102-06-9) → 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone (866102-07-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 8h; Heating;

DOI:10.1055/s-2005-871925

Reference yield:

3-bromo-2-chloromethylthiophene → 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone (866102-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / t-BuOK / 2-methyl-propan-2-ol / 12 h / Heating

2: 48 percent / aq. KOH / ethanol / 8 h / Heating

With potassium hydroxide; potassium tert-butylate; In ethanol; tert-butyl alcohol;

DOI:10.1055/s-2005-871925

Reference yield:

4-carbethoxy-3-methyl-2-cyclohexen-1-one (487-51-4) → 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone (866102-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / t-BuOK / 2-methyl-propan-2-ol / 12 h / Heating

2: 48 percent / aq. KOH / ethanol / 8 h / Heating

With potassium hydroxide; potassium tert-butylate; In ethanol; tert-butyl alcohol;

DOI:10.1055/s-2005-871925

upstream raw materials:

3-(3-bromo-furan-2-ylmethyl)-2-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester

4-carbethoxy-3-methyl-2-cyclohexen-1-one

Downstream raw materials:

2-(3-bromo-furan-2-ylmethyl)-3,3-dimethyl-cyclohexanone

3-bromo-2-(2,2-dimethyl-6-methylenecyclohexylmethyl)furan

Refernces

Heteroaryl radicals: A furyl radical in the synthesis of the tricyclic framework of eremophilane sesquiterpenoids

10.1055/s-2005-871925

The research investigates the intramolecular addition of thieno and furan radicals to alkenyl groups, resulting in the formation of a linearly annulated tricyclic moiety through a 6-endo-trig selective cyclization process. Key chemicals involved in the study include 2-bromo-3-bromomethyl thiophene derivatives, which serve as radical precursors. The desired alkene 6 is derived from Hagemann’s ester 1 through a series of reactions involving t-BuOK, KOH, Me2CuLi, and Ph3P+CH3I–. The radical cyclization of 6 in refluxing benzene with Bu3SnH and a catalytic amount of AIBN yields 5,5-dimethyl-4,4a,5,6,7,8,8a,9-octahydro-naphtho[2,3-b]thiophene (7). For furan derivatives, 3-bromo-2-chloromethylfuran is used to synthesize compound 9, which is then converted to 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone (10) and further to 3-bromo-2-(2,2-dimethyl-6-methylenecyclohexylmethyl)furan (12). The radical cyclization of 12 with Bu3SnH and AIBN results in the formation of 8,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3b]furan (13). The study demonstrates the potential of using radical reactions to synthesize tricyclic frameworks, particularly for furanoeremophilane sesquiterpenoids, and explores the general applicability of this approach for creating new ring-fused heterocyclic structures.