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

Base Information

Chemical Name:(-)-2,4-dibromo-5-{(Z)-[(1S,3aS,4S,7aS)-1-tert-butoxy-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-yl]vinyl}benzaldehyde
CAS No.:446265-70-9
Molecular Formula:C₂₃H₂₈Br₂O₂
Molecular Weight:496.282
Hs Code.:

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

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

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

There total 5 articles about (-)-2,4-dibromo-5-{(Z)-[(1S,3aS,4S,7aS)-1-tert-butoxy-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-yl]vinyl}benzaldehyde 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: 83.0%

: 446265-62-9
(-)-(1S,3aS,4S,7aS)-1-tert-butoxy-4-{(Z)-2-[2,4-dibromo-5-([1,3]dioxolan-2-yl)phenyl]vinyl}-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-indene

: 446265-70-9
(-)-2,4-dibromo-5-{(Z)-[(1S,3aS,4S,7aS)-1-tert-butoxy-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-yl]vinyl}benzaldehyde

Guidance literature:: With pyridinium p-toluenesulfonate; In acetone; for 108h; Heating;
DOI:10.1002/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4

Reference yield:

: 97094-37-6
2,4-dibromobenzene-1,5-dicarboxaldehyde

: 446265-70-9
(-)-2,4-dibromo-5-{(Z)-[(1S,3aS,4S,7aS)-1-tert-butoxy-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-yl]vinyl}benzaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 26 percent / p-TsOH*H₂O / toluene / 1.5 h / Heating

2.1: PPh₃ / CH₂Cl₂ / -20 °C

2.2: 80 percent / p-TsOH*H₂O / toluene / 5 h / Heating

3.1: 92 percent / n-Bu₃SnH / [Pd(PPh₃)4] / toluene / 1.5 h / 20 °C

4.1: 50 percent / aq. n-Bu₄NOAc; PPh₃ / Pd(OAc)2 / dimethylformamide; acetonitrile / 21 h / 60 °C

5.1: 83 percent / aq. pyridinium p-toluenesulfonate / acetone / 108 h / Heating

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 4.1: Heck reaction;
DOI:10.1002/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4

Reference yield:

: 446265-59-4
2,4-dibromo-5-[1,3]dioxolan-2-ylbenzaldehyde

: 446265-70-9
(-)-2,4-dibromo-5-{(Z)-[(1S,3aS,4S,7aS)-1-tert-butoxy-7a-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-yl]vinyl}benzaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPh₃ / CH₂Cl₂ / -20 °C

1.2: 80 percent / p-TsOH*H₂O / toluene / 5 h / Heating

2.1: 92 percent / n-Bu₃SnH / [Pd(PPh₃)4] / toluene / 1.5 h / 20 °C

3.1: 50 percent / aq. n-Bu₄NOAc; PPh₃ / Pd(OAc)2 / dimethylformamide; acetonitrile / 21 h / 60 °C

4.1: 83 percent / aq. pyridinium p-toluenesulfonate / acetone / 108 h / Heating

With tri-n-butyl-tin hydride; tetrabutylammonium acetate; pyridinium p-toluenesulfonate; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Heck reaction;
DOI:10.1002/1521-3765(20020503)8:9<2116::AID-CHEM2116>3.0.CO;2-4