Réaction #1552105

Équation de réaction

2,7-dibromophenazine

tributyl(1-ethoxyvinyl)stannane

→

2,7-bis(1-ethoxyvinyl)phenazine

Rendement 88.1%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   AutreThe crude reaction mixture
2. 2
   Filtrationwas filtered through CELITE™ 545
3. 3
   Autrethe volatiles were removed in vacuo
4. 4
   AutreThe crude brown solid was triturated with isohexanes
5. 5
   Filtrationfiltered

Mode opératoire

To a solution of 2,7-dibromophenazine (13-2) (1.52 g, 4.50 mmol) in dry dioxane (75 mL) under N2 was added tributyl(1-ethoxyvinyl)stannane (3.34 ml, 9.89 mmol) and Pd(dppf)Cl2 (0.316 g, 0.450 mmol). The resultant mixture was heated at 100° C. for 4 hrs in a sealed tube. The crude reaction mixture was filtered through CELITE™ 545, and the volatiles were removed in vacuo. The crude brown solid was triturated with isohexanes and filtered to give 2,7-bis(1-ethoxyvinyl)phenazine as a brown solid (1.27 g, 88% yield). 1H NMR (CDCl3): δ 8.55-8.53 (2H, m), 8.19-8.15 (2H, m), 8.11-8.07 (2H, m), 4.98 (2H, d, J=3 Hz), 4.49 (2H, d, J=3 Hz), 4.03 (4H, q, J=7 Hz), 1.50 (6H, t, J=7 Hz) ppm. LC-MS (ESI): m/z 322.1 [M+H]+.

Source