(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

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Chemical Name:(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne
CAS No.:619309-04-5
Molecular Formula:C₂₅H₂₉Br₂ClSi₂
Molecular Weight:580.937
Hs Code.:

Synonyms:(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

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Chemical Property of (E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

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Technology Process of (E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

There total 3 articles about (E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne 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: 84.0%

: 558-13-4
carbon tetrabromide

: 619308-98-4
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-pent-3-en-1-yn-5-al

: 619309-04-5
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

Guidance literature:: carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-pent-3-en-1-yn-5-al; In dichloromethane; for 1h; Further stages.;
DOI:10.1039/b707681a

Reference yield:

: 619308-84-8
5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne

: 619309-04-5
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

Guidance literature:: Multi-step reaction with 3 steps

1.1: Me₃SnLi; CuBr*Me₂S complex / tetrahydrofuran / -50 - 20 °C

1.2: n-BuLi / tetrahydrofuran; hexane / 4 h / -78 °C

1.3: CuCl₂ / tetrahydrofuran / 0 - 20 °C

2.1: 89 percent / MnO₂ / CH₂Cl₂ / 5 h / 20 °C

3.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 76 percent / CH₂Cl₂ / 1.5 h / 0 °C

With (trimethylstannyl)lithium; manganese(IV) oxide; copper(I) bromide dimethylsulfide complex; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1.2: 1,4-retro-Brook rearrangement;
DOI:10.1021/ol035536e

Reference yield:

: 619308-94-0
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-1-(trimethylsilyl)-pent-3-en-1-yn-5-ol

: 619309-04-5
(E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / MnO₂ / CH₂Cl₂ / 5 h / 20 °C

2.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 76 percent / CH₂Cl₂ / 1.5 h / 0 °C

With manganese(IV) oxide; triphenylphosphine; In dichloromethane;
DOI:10.1021/ol035536e