Réaction #11038

Équation de réaction

2,7-dibromo-3,6-di-t-butylfluorene

phenylboronic acid

Na2CO3

→

2,7-diphenyl-3,6-di-t-butyl-fluorene

Rendement 179.4%

Solvants

toluene

water

EtOH

Conditions de réaction

Traitement

1. 1
   Températureunder reflux
2. 2
   AutreThe reaction mixture was quenched with water
3. 3
   Extractionextracted with ether
4. 4
   Séchagedried over MgSO4
5. 5
   Autreevaporated under vacuum
6. 6
   Autreto produce a residue which
7. 7
   Autrewas purified by column chromatography (silica gel, hexane/CH2Cl2=5/1)

Mode opératoire

To a mixture of 2,7-dibromo-3,6-di-t-butylfluorene (0.96 g, 2.20 mmol) and Pd(PPh3)4 (260 mg, 0.22 mmol) in toluene (50 ml) was added a solution of phenylboronic acid (0.81 g, 6.63 mmol) in EtOH (10 ml) and a solution of Na2CO3 (1.5 g) in water (10 ml). The reaction mixture was stirred for 6 hours under reflux. The reaction mixture was quenched with water, extracted with ether, dried over MgSO4, and evaporated under vacuum to produce a residue which was purified by column chromatography (silica gel, hexane/CH2Cl2=5/1) to yield 2,7-diphenyl-3,6-di-t-butyl-fluorene (0.85 g, 90%). 1H NMR (CDCl3): δ 7.96 and 7.15 (each s, 2H, 1,8- and 4,5-H (Flu), 7.33 (m, 10H, Ph), 3.77 (s, 2H, H9), 1.27 (s, 18H, t-Bu).

Source