Phenol → 9-Phenoxyacridine

Participants

Reaction Conditions

Reaction Steps

Dry benzene (450 mL) was added to 1.50 g acridone (1 equiv.) under N2-atmosphere. SOCl2 (3.37 mL, 6 equiv.) was added and the reaction mixture was refluxed over night followed by removal of solvent by evaporation. Dry DMF (75 mL), phenol (2.17 g, 3 equiv.) and K2CO3 (4.26 g, 3 equiv.) were added under N2. The reaction was stirred at 60° C. for 3.5 days. After filtration and evaporation the crude product was purified using flash chromatography (CH2Cl2 to CH2Cl2:Et2O, 6:1) giving 2.04 g of 2, 98% yield. 1H NMR (CDCl3): 8.28 (5+4, br ddd, J=8.9, 1.1, 0.8 Hz, 2H), 8.11 (8+1, ddd, J=8.7, 1.3, 0.8 Hz, 2H), 7.79 (6+3, ddd, J=8.9, 6.6, 1.3 Hz, 2H), 7.47 (7+2, ddd, J=8.7, 6.6, 1.1 Hz, 2H), 7.28 (2′+4′, m, 2H), 7.06 (3′, m, 1H), 6.86 (1′+5′, m, 2H). 3.40 (6, m, 2H).

Provenance & Evidence