ChemicalBook CAS DataBase List 4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE

4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE synthesis

5synthesis methods

Product Name:4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE
CAS Number:117567-53-0
Molecular formula:C19H31Br
Molecular Weight:339.35

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Yield:-

Steps:

Multi-step reaction with 8 steps
1: 1.) EtMgBr, 2.) CuBr / 1.)THF, reflux, 1 h, 2.) THF, reflux, 12 h
2: 87 percent / H₂, ethylenediamine / P-2 nickel / ethanol / 4 h / 760 Torr
3: 97 percent / 50percent aq. TFA / CH₂Cl₂ / 3 h / 0 °C
4: 80 percent / PPh₃ / CH₂Cl₂ / 1 h / 0 °C
5: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.5 h / -78 - 0 °C
6: 1.) EtMgBr, 2.) CuBr / 1.) THF, reflux, 10 min, 2.) THF, reflux, 12 h
7: 65 percent / H₂ / P-2 nickel / ethanol / 5 h
8: 76 percent / CBr₄, PPh₃ / CH₂Cl₂ / 10 h / Ambient temperature

References:

Heitz, Marie-Paule;Wagner, Alain;Mioskowski, Charles;Noel, Jean-Pierre;Beaucourt, Jean-Pierre [Journal of Organic Chemistry,1989,vol. 54,# 2,p. 500 - 503]