Potassium Carbonate → 1-Chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthalene

Participants

Reaction Steps

To a mixture containing 28.02 g (0.203 mole) of anhydrous potassium carbonate and 30.26 g (0.134 mole) of 3,4,5-trichloro-1-nitrobenzene in 300 ml dry DMF under an atmosphere of nitrogen and at room temperature was added 30.04 g (0.168 mole) of 4-chloro-1-naphthol. The flask was then placed in an oil bath which was heated. An internal reaction temperature of 105° C. was reached and maintained for 20 hours. After cooling the reaction mixture to room temperature most of the DMF was removed under vacuum. The residue was taken up in 1.5 L of 1:1 EtOAc to Et2O and 300 ml of H2O. The layers were separated and washed twice with 5% NaOH, twice with H2O, and finally once with a saturated aqueous NaCl solution. After drying over anhydrous Na2SO4 removal of the solvents afforded 48.73 g of a dark brown solid. This was recrystallized twice from hexane-ethyl acetate to afford 15.84 g of pale yellow needles; mp 121.5°-123° C. NMR (COCl3): δ6.18 (d, J=8 Hz, 1H), 7.25 (d, J=8 Hz 1H) 8.4-8.7 (m, 2H), 8.0-8.5 (m, 4H, contains 8.25 [S]).

Provenance & Evidence