Dichloromethane → 2,4-Dichloro-1-(2-nitrophenoxy)benzene

Participants

Reaction Steps

2,4-dichlorophenol (3.0 g, 18.4 mmol), 2-fluoro-1-nitrobenzene (1.28 ml, 12.1 mmol) and potassium carbonate (3.0 g, 22.1 mmol) were mixed in DMF (10 ml) and heated at reflux for 3 h. DMF removed in-vacuo. NaOH (1M) added, and extracted with diethyl ether, organic layers dried over MgSO4 and evaporated to dryness, to afford a yellow solid. 3.7 g, >100%, m.p. 54-55° C., Rf. 0.80 (DCM), LCMS tr=5.02 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 283.06, 285.07, HPLC tr=2.39 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 99.75%, 1HNMR (CDCl3, 270 MHz) δ 6.86 (1H, dd, J=1.2, 8.4 Hz, ArH), 6.98 (1H, d, J=6.9 Hz, ArH), 7.23 (1H, m, ArH), 7.23 (1H, m, ArH), 7.50 (1H, m, ArH), 7.50 (1H, m, ArH), 7.98 (1H, dd, J=1.5, 8.2 Hz, ArH).

Provenance & Evidence