[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

Base Information

Chemical Name:[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide
CAS No.:80206-27-5
Molecular Formula:Br*C₃₈H₄₂OPSi
Molecular Weight:653.714
Hs Code.:

Synonyms:[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

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Chemical Property of [3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

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Technology Process of [3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

There total 7 articles about [3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide 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:

: 58556-75-5
2,7-dibromonaphthalene

: 80206-27-5
[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, -55 deg C

2: 61 percent / MnO₂ / CH₂Cl₂

3: 79 percent / conc. H₂SO₄

4: 1.) LiEt₃BH, 2.) imidazole / 1.) THF, 2.) DMF

5: 1.) n-BuLi / 1.) THF, -55 deg C, 2.) -70 deg C

6: 1.) DIBAL-H, 2.) (n-C₈H₁₇)3P, CBr₄ / 1.) hexane, 2.) ether, 3.) benzene, 80 deg C

With 1H-imidazole; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; TOP; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; In dichloromethane;
DOI:10.1021/ja00365a087

Reference yield:

: 582-17-2
2,7-Dihydroxynaphthalene

: 80206-27-5
[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

Guidance literature:: Multi-step reaction with 7 steps

1: 41 percent / Ph₃PBr₂ / 320 °C

2: 1.) n-BuLi / 1.) THF, -55 deg C

3: 61 percent / MnO₂ / CH₂Cl₂

4: 79 percent / conc. H₂SO₄

5: 1.) LiEt₃BH, 2.) imidazole / 1.) THF, 2.) DMF

6: 1.) n-BuLi / 1.) THF, -55 deg C, 2.) -70 deg C

7: 1.) DIBAL-H, 2.) (n-C₈H₁₇)3P, CBr₄ / 1.) hexane, 2.) ether, 3.) benzene, 80 deg C

With 1H-imidazole; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; TOP; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; triphenylphosphine dibromide 1:1 addition complex; In dichloromethane;
DOI:10.1021/ja00365a087

Reference yield:

: 80206-23-1
1-(7-Bromo-naphthalen-2-yl)-prop-2-en-1-ol

: 80206-27-5
[3-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydro-1H-cyclopenta[a]naphthalen-8-ylmethyl]-triphenyl-phosphonium; bromide

Guidance literature:: Multi-step reaction with 5 steps

1: 61 percent / MnO₂ / CH₂Cl₂

2: 79 percent / conc. H₂SO₄

3: 1.) LiEt₃BH, 2.) imidazole / 1.) THF, 2.) DMF

4: 1.) n-BuLi / 1.) THF, -55 deg C, 2.) -70 deg C

5: 1.) DIBAL-H, 2.) (n-C₈H₁₇)3P, CBr₄ / 1.) hexane, 2.) ether, 3.) benzene, 80 deg C

With 1H-imidazole; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; TOP; sulfuric acid; diisobutylaluminium hydride; lithium triethylborohydride; In dichloromethane;
DOI:10.1021/ja00365a087