Sodium Carbonate → HCID 68599131, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)benzonitrile was prepared through the following procedure. A mixture of 2,7-dibromo-9,9-dihexyl-9H-fluorene (0.985 g, 2 mmol), 4-cyanophenylboronic acid (0.146 g, 1 mmol), and tetrakis(triphenylphosphine) palladium (11.6 mg, 0.01 mmol) were added to an air-free two-phase mixture of toluene (25 mL) and aqueous 2M Na2CO3 solution (15 mL). The resulting mixture was vigourously stirred under argon atmosphere at 110° C. for 24 hours. The organic layer was separated and the aqueous phase was extracted with ether. The organic layers were washed with brine (2×50 mL), and dried with anhydrous MgSO4. The solvent was evaporated and the residue passed through a silica-gel column. 0.27 g of pure product were obtained by recrystallization in heptane with a yield of 51%. 1H NMR (400 MHz, CDCl3): δ(ppm) 7.766-7.751 (m, 5H), 7.605-7.583 (d, J=8.8 Hz, 1H), 7.583-7.564 (d, J=7.6 Hz, 1H), 7.524 (s, 1H), 7.495-7.476 (m, 2H), 2.013-1.964 (m, 4H), 1.140-1.053 (m, 12H), 0.781-0.746 (t, J=7.0 Hz, 6H), 0.658-0.624 (m, 4H).

Provenance & Evidence