2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

Base Information

Chemical Name:2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone
CAS No.:333385-24-3
Molecular Formula:C₂₁H₂₇BrO₃
Molecular Weight:407.348
Hs Code.:

Synonyms:2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

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Chemical Property of 2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

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Technology Process of 2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

There total 9 articles about 2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone 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: 37.0%

: 333385-07-2
3-bromo-2-[3-(6,6-dimethyl-cyclohex-1-enyl)-1-methyl-propyl]-5-methoxy-benzofuran

: 333385-24-3
2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

Guidance literature:: 3-bromo-2-[3-(6,6-dimethyl-cyclohex-1-enyl)-1-methyl-propyl]-5-methoxy-benzofuran; With dimethylsulfide borane complex; In diethyl ether; dichloromethane; at 20 ℃; for 18h;

With sodium hydroxide; dihydrogen peroxide; In diethyl ether; ethanol; dichloromethane; at 0 - 20 ℃; for 3h;

With jones reagent; In acetone; for 0.5h; Further stages.;
DOI:10.1021/ja0021060

Reference yield:

: 263862-76-6
3-bromo-5-methoxy-benzofuran-2-carboxylic acid 3,3-dimethyl-2-methylene-cyclohexyl ester

: 333385-24-3
2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / toluene; tetrahydrofuran / 1 h / 0 - 20 °C

2.1: 2.66 g / toluene / 1 h / Heating

3.1: 78 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

4.1: 86 percent / zinc iodide; sodium cyanoborohydride / 1,2-dichloro-ethane / 2.5 h / Heating

5.1: borane dimethylsulfide complex / CH₂Cl₂; diethyl ether / 18 h / 20 °C

5.2: aq. NaOH; aq. H₂O₂ / diethyl ether; CH₂Cl₂; ethanol / 3 h / 0 - 20 °C

5.3: 37 percent / Jones reagent / acetone / 0.5 h

With pyridine; dimethylsulfide borane complex; sodium cyanoborohydride; zinc(II) iodide; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene; 2.1: Claisen rearrangement;
DOI:10.1021/ja0021060

Reference yield:

: 333385-05-0
3-bromo-5-methoxybenzofuran-2-carboxylic acid

: 333385-24-3
2-[3-(3-bromo-5-methoxy-benzofuran-2-yl)-butyl]-3,3-dimethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-toluenesulfonyl chloride / pyridine / 0.33 h / 0 °C

1.2: 78 percent / pyridine / 1 h / 0 °C

2.1: pyridine / toluene; tetrahydrofuran / 1 h / 0 - 20 °C

3.1: 2.66 g / toluene / 1 h / Heating

4.1: 78 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5.1: 86 percent / zinc iodide; sodium cyanoborohydride / 1,2-dichloro-ethane / 2.5 h / Heating

6.1: borane dimethylsulfide complex / CH₂Cl₂; diethyl ether / 18 h / 20 °C

6.2: aq. NaOH; aq. H₂O₂ / diethyl ether; CH₂Cl₂; ethanol / 3 h / 0 - 20 °C

6.3: 37 percent / Jones reagent / acetone / 0.5 h

With pyridine; dimethylsulfide borane complex; sodium cyanoborohydride; p-toluenesulfonyl chloride; zinc(II) iodide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene; 3.1: Claisen rearrangement;
DOI:10.1021/ja0021060