Methyl iodide → 9-Methylfluorene

Participants

Reaction Steps

To a solution of fluorene (10.0 g, 60.0 mmol) in 100 mL of THF was added n-BuLi (66.6 mmol) at -78° C. This solution was then added to a chilled solution of iodomethane (15.04 g, 90.6 mmol) in 60 mL of THF. The temperature was kept at about -20° C. to maintain a clear solution. The mixture was allowed to warm to room temperature and then quenched with saturated aqueous NH4Cl and evaporated to a residue which was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with MgSO4, filtered and evaporated to a solid. This solid was dissolved with hot pentane, stirred with decolorizing charcoal, filtered through a celite pad, and evaporated to get 10.0 g(92%) of 9-methyl fluorene was a white solid, mp 42°-43° C. FT-IR (KBr): 3065, 3039, 3016, 2962, 2926, 2864, 1478, 1445, 1309, 1023, 792 cm-1. NMR (300 MHz, CHCl3) δ 1.60-1.62(d, 3H, J=7.5 Hz), 3.93-3.97 (q, 1H, J=7.5 Hz), 7.32-7.38 (m, 4H) , 7.35-7.36 (d, 2H, J=8.0 Hz), 7.81-7.83(d, 2H, J=8.0 Hz).

Provenance & Evidence