2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

Base Information

Chemical Name:2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde
CAS No.:914933-62-3
Molecular Formula:C₂₄H₃₉BrO₆Si
Molecular Weight:531.56
Hs Code.:

Synonyms:2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

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Chemical Property of 2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

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Technology Process of 2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

There total 10 articles about 2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-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: 81.0%

: 914933-67-8
{2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-phenyl}-methanol

: 914933-62-3
2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1021/ol0617291

Reference yield:

: 56518-42-4
4-bromo-3,5-dimethoxybenzoic acid

: 914933-62-3
2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 40 °C

2: 100 percent / imidazole; 4-DMAP / CH₂Cl₂ / 20 °C

3: 67 percent / t-BuLi / pentane; tetrahydrofuran / -78 - 20 °C

4: 94 percent / imidazole; 4-DMAP / dimethylformamide / 20 °C

5: 100 percent / NBS / acetonitrile / 1.5 h / 20 °C

6: 100 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

7: 81 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane; 7: Swern oxidation;
DOI:10.1021/ol0617291

Reference yield:

: 5754-32-5
2-(2-methyl-1,3-dioxolan-2-yl)ethanol

: 914933-62-3
2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.75 h / -78 - -20 °C

2: 67 percent / t-BuLi / pentane; tetrahydrofuran / -78 - 20 °C

3: 94 percent / imidazole; 4-DMAP / dimethylformamide / 20 °C

4: 100 percent / NBS / acetonitrile / 1.5 h / 20 °C

5: 100 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

6: 81 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane; 6: Swern oxidation;
DOI:10.1021/ol0617291