Dimethyl Sulfoxide → 2-iodo-9,9-dimethyl-9H-fluorene

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Reaction Steps

A 500 mL round bottomed flask was charged with 21.8 g (70 mmol) 2-Iodofluorene and 1.18 g (5 mmol) benzyltriethylammonium chloride. 200 mL of dimethylsulfoxide (DMSO) was then added followed by 28 mL (50%) NaOH. The mixture was allowed to stir under nitrogen for 1 hour, before 29 g (210 mmol) methyl iodide was added through the septum. The mixture was allowed to stir at room temperature for 18 hours. After cooling to ambient temperature the mixture was transferred to a 1 L separatory funnel. 100 mL of water and 100 mL of diethylether were added to the mixture. The organic layer was collected and the aqueous layer was extracted with diethyl ether (4×100 mL). The organic fractions were combined, dried over anhydrous magnesium sulfate, and the solvent evaporated under vacuo. A flash column was then performed using hexanes as the eluent to give 21.0 g (88% yield) of the product (yellow oil).

Provenance & Evidence