(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Base Information

• Chemical Name: (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene
• CAS No.: 345222-84-6
• Molecular Formula: C₂₄H₂₉Br₃O
• Molecular Weight: 573.206
• Mol file: 345222-84-6.mol

Synonyms:(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Chemical Property of (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

There total 9 articles about (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene 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: 88.0%

(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-(2,2-dibromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene (345295-27-4) → (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene (345222-84-6)

Guidance literature:

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 ℃; for 2h;

DOI:10.1055/s-2001-12438

Reference yield:

2,5-dibromoterephthalaldehyde (63525-48-4) → (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene (345222-84-6)

Guidance literature:

Multi-step reaction with 7 steps

1: PPh₃ / CH₂Cl₂ / 0.5 h / -20 °C

2: pTsOH / toluene / 1.5 h / Heating

3: 98 percent / Bu₃SnH / Pd(PPh₃)4 / toluene / 1 h / 20 °C

4: 41 percent / PPh₃; nBu₄NOAc / Pd(OAc)2 / dimethylformamide; acetonitrile; H₂O / 16 h / 60 °C

5: 74 percent / aq. HOAc / 2 h / 80 °C

6: 90 percent / PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

7: 88 percent / HSnBu₃ / Pd(PPh₃)4 / toluene / 2 h / 20 °C

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Corey-Fuchs reaction / 4: Heck reaction / 6: Corey-Fuchs reaction;

DOI:10.1055/s-2001-12438

Reference yield:

1,4-dibromo-2-(2,2-dibromovinyl)-5-[1,3]dioxolan-2-ylbenzene (345222-81-3) → (-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-((Z)-2-bromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene (345222-84-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / n-Bu₃SnH / [Pd(PPh₃)4] / toluene / 1.5 h / 20 °C

2.1: 41 percent / aq. n-Bu₄NOAc; PPh₃ / Pd(OAc)2 / dimethylformamide; acetonitrile / 21 h / 60 °C

3.1: 74 percent / aq. AcOH / 2 h / 80 °C

4.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 90 percent / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 88 percent / n-Bu₃SnH / [Pd(PPh₃)4] / toluene / 1.5 h / 20 °C

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; acetic acid; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Heck reaction / 4.2: Corey-Fuchs reaction;

DOI:10.1002/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4

upstream raw materials:

(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,5-dibromo-4-(2,2-dibromovinyl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

tert-butyl (1S,3aS,7aS)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-yl ether

2,5-dibromo-4-[1,3]dioxolan-2-ylbenzaldehyde

1,4-dibromo-2-[(Z)-2-bromovinyl]-5-[1,3]dioxolan-2-ylbenzene