3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene

Base Information

• Chemical Name: 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene
• CAS No.: 858946-81-3
• Molecular Formula: C₃₀H₃₉Br₂FO₂Si₂
• Molecular Weight: 666.616

Synonyms:3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene

Chemical Property of 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene

There total 11 articles about 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene 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: 92.0%

3-[[tert-butyl(dimethyl)silyl]oxy]-7-(4-[[tert-butyl(dimethyl)silyl]oxy]-3-fluorophenyl)-1-naphthaldehyde (858946-79-9) + carbon tetrabromide (558-13-4) → 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene (858946-81-3)

Guidance literature:

With triphenylphosphine; zinc; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jm058173s

Reference yield:

7-Methoxy-1-tetralone (6836-19-7) → 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene (858946-81-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: ZnI₂ / benzene / 20 °C

1.2: POCl₃; pyridine / benzene / 6 h / Heating

2.1: p-cymene / Pd/C / Heating

3.1: 0.88 g / C₆H₅N*HCl / 2 h / 190 °C

4.1: Br₂; acetic acid / 6 h / 100 °C

4.2: aq. HCl; SnCl₂ / 1 h / 100 °C

5.1: 2.17 g / CuBr / dimethylformamide; methanol / 3 h / Heating

6.1: 94 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 73 percent / aq. Na₂CO₃; Pd[P(Ph)3]4 / 1,2-dimethoxy-ethane / 85 °C

8.1: 88 percent / C₆H₅N*HCl / 2 h / 190 °C

9.1: 59 percent / imidazole / dimethylformamide

10.1: 49 percent / DIBAL / toluene / -78 - 20 °C

11.1: 92 percent / zinc; PPh₃ / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4-methylisopropylbenzene; C₆H₅N*HCl; bromine; diisobutylaluminium hydride; sodium carbonate; acetic acid; triphenylphosphine; copper(I) bromide; zinc(II) iodide; zinc; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 7.1: Suzuki coupling;

DOI:10.1021/jm058173s

Reference yield:

7-methoxy-3,4-dihydronaphthalene-1-carbonitrile (158365-53-8) → 3-(tert-butyldimethylsilanyloxy)-7-[4-(tert-butyldimethylsilanyloxy)-3-fluorophenyl]-1-(2,2-dibromovinyl)naphthalene (858946-81-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: p-cymene / Pd/C / Heating

2.1: 0.88 g / C₆H₅N*HCl / 2 h / 190 °C

3.1: Br₂; acetic acid / 6 h / 100 °C

3.2: aq. HCl; SnCl₂ / 1 h / 100 °C

4.1: 2.17 g / CuBr / dimethylformamide; methanol / 3 h / Heating

5.1: 94 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 73 percent / aq. Na₂CO₃; Pd[P(Ph)3]4 / 1,2-dimethoxy-ethane / 85 °C

7.1: 88 percent / C₆H₅N*HCl / 2 h / 190 °C

8.1: 59 percent / imidazole / dimethylformamide

9.1: 49 percent / DIBAL / toluene / -78 - 20 °C

10.1: 92 percent / zinc; PPh₃ / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4-methylisopropylbenzene; C₆H₅N*HCl; bromine; diisobutylaluminium hydride; sodium carbonate; acetic acid; triphenylphosphine; copper(I) bromide; zinc; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Suzuki coupling;

DOI:10.1021/jm058173s

upstream raw materials:

3-[[tert-butyl(dimethyl)silyl]oxy]-7-(4-[[tert-butyl(dimethyl)silyl]oxy]-3-fluorophenyl)-1-naphthaldehyde

carbon tetrabromide

3-bromo-7-hydroxy-1-cyanonaphthalene

7-hydroxy-3-methoxy-1-naphthonitrile

Downstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-7-[4-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-phenyl]-1-ethynyl-naphthalene

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