1,3-Dibromopropane → HCID 68581877, compound

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Reaction Steps

Powdered KOH (983 mg, 17.5 mmol) was added in batches over 1 minute to a heterogeneous mixture of 2,7-dibromo-9H-fluorene (1.31 g, 4.04 mmol) and 1,3-dibromopropane (837 mg, 4.15 mmol) in DMSO (20 mL), and stirred at ambient condition for ˜5 days. The mixture was diluted with water (200 mL) and extracted with 10% CH2Cl2/hexanes (100 mL, 2×). The combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified with a column chromatography (sample was loaded as a silica gel mesh; hexanes, with gravity elution) to afford 2′,7′-dibromospiro[cyclobutane-1,9′-fluorene] as a white fluffy solid (600 mg). 1H NMR (CDCl3, δ=7.24, 400 MHz): 7.86 (d, J=1.8, 2H), 7.48 (d, J=8.0, 2H), 7.44 (dd, J=8.1, 1.8, 2H), 2.61 (app t, J=8.1, 4H), 2.42-2.34 (m, 2H).

Provenance & Evidence