Fluorene → HCID 178506660, compound

Participants

Reaction Steps

To a solution of 10.38 g (62.5 mmol) of fluorene in 250 ml of THF at 0° C. was added dropwise a 1.6 molar solution of butyllithium in hexane (39.05 ml, 62.5 mmol) in order to produce fluorenyllithium. The solution was stirred for 3 h at room temperature and then added dropwise over a period of 2 h via a cannula to 125 ml (1.45 mol) of 1,2-dibromoethane. The solution was stirred overnight at room temperature. After hydrolysis with 125 ml aqueous NH4Cl, the organic layer was separated. The aqueous layer was extracted twice with ether. The combined organic layers were dried on MgSO4, filtered and the solvents were removed. The excess 1,2-dibromoethane was recovered by trap to trap distillation at 0.5 mm Hg with gentle heating by a warm water bath. A chilled receiving flask was used. The resulting yellow residue was dissolved in pentane, filtered, concentrated and cooled to -20° C. to give 1-(9-fluorenyl)-2-bromoethane (10.25 g, 60%) as a yellow solid; melting point: 48-49° C. 1H NMR data was consistent with that reported in literature.

Provenance & Evidence