Figure 3.11 Synthesis of 9,9-dioctylfluorene (Source: Ranger et al., 1997). 42.92 mL of n-butyllithium (107.31 mmol, 2.5 M in hexane) was added dropwise into a ...
Alkylation of fluorene.
C8H17
C8H17
Figure 3.11 Synthesis of 9,9-dioctylfluorene (Source: Ranger et al., 1997).
42.92 mL of n-butyllithium (107.31 mmol, 2.5 M in hexane) was added dropwise into a -78oC solution that contains 8.48 g of fluorene (51.1 mmol) in 120 mL of THF. The temperature of the solution mixture was controlled at -78oC and stirred for 45 minutes before another portion of THF mixture. This second portion of THF (25 mL) consists of octyl bromide (22.70 g, 117.53 mmol) was added dropwise into the former solution mixture. The resulting mixture was warmed to room temperature and continue stirred for another 3 hours. After that, addition of distilled water followed by ether extraction. The collected organic layers were combined and washed with brine, after which dried over MgSO4. The resulting solvent was then removed under reduced pressure and the excess octyl bromide present in the solvent was separated via distillation (44oC, 0.3 mmHg). Finally, the obtained 9,9-dioctylfluorene (pale-brown powder) was purified via silica TLC with hexane effluent and further identified by 13C-NMR and 1H-NMR (Ranger et al., 1997).
