Potassium Carbonate → HCID 59848141, compound

Participants

Reaction Steps

3,5-dibromophenol (970 mg, 3.85 mmol) was recrystallized from hexanes. After removal of solvent, N-(4-bromobutyl)phthalimide (1.38 g, 4.89 mmol), K2CO3 (1.88 g, 13.6 mmol), 18-crown-6 (53 mg, 0.20 mmol), and acetone (20 mL) were added. This was refluxed for 1 hour, and then poured into 100 mL of water. The aqueous layer was extracted with dichloromethane (4×30 mL). The organic layers were combined, washed with water, saturated NaHCO3, and brine, then dried over MgSO4 and filtered. Removal of solvent yielded a white solid, which was purified by column chromatography (4:1 hexanes:CH2Cl2) followed by recrystallization in hexanes to yield colorless needles (650 mg, 87%). 1H NMR (CDCl3): 7.860 (m, 2H); 7.733 (m, 2H); 7.220 (t, J=1.6 Hz, 1H); 6.964 (d, J=2.0 Hz, 2H); 3.962 (t, J=6.0 Hz, 2H); 3.770 (t, J=6.6 Hz, 2H); 1.846 (m, 4H).

Provenance & Evidence