Fluorene → HCID 22407026, compound

Participants

Reaction Steps

A solution of fluorene (5.04 g; 30.32 mmol) in THF (50 mL) was cooled to 0° C. and treated with n-butyllithium (12.13 mL of a 2.5M solution in hexanes; 30.32 mL). After stirring the resulting dark red mixture for 20 minutes, a solution of 2-(2-bromoethyl)-1,3-dioxolane (6.03 g; 33.35 mmol) in 20 mL of THF was added, and the resulting mixture was stirred overnight, allowing it to come to room temperature. It was quenched by the addition of saturated ammonium chloride (50 mL) and extracted into ethyl acetate (50 mL). The organic phase was washed with brine, dried and freed of solvent. The crude residue was purified on a flash chromatography column, eluting with 20% ethyl acetate in hexane, to obtain 5.74 g (72%) of the product as an oil. 1H NMR (CDCl3): δ 1.43 (m, 2H); 2.18 (m, 2H); 3.82, 3.86 (m, 2H each); 4.15 (t, 1H); 4.77 (t, 1H); 7.31 (m, 4H); 7.51 (dd, 2H); 7.68 (dd, 2H).

Provenance & Evidence