Dichloromethane → Methyl 2-[(4-chloro-2-nitrophenyl)thio]benzoate

Participants

Reaction Steps

To a mixture of 5-chloro-2-nitrofluorobenzene (176 mg, 1 mmol) and methyl thiosalicylate (275 μL, 2 mmol) in DMF (5 mL) was added Cs2CO3 (652 mg, 2 mmol) and the resulting mixture was stirred at room temperature for 2 h. The mixture was diluted with CH2Cl2, washed with water, dried (Na2SO4), concentrated and flash chromatographed (SiO2, heptane:toluene, 1:10-1:4) to give 300 mg (92%) of the title compound (189JO09). 1H NMR (CDCl3) δ 8.15 (d, 1 H J=2.4 Hz), 7.94 (m, 1 H), 7.53-7.46 (m, 3 H), 7.34 (dd, 1 H, 2.4, 8.6 Hz), 6.95 (d, 1 H, J=8.8 Hz), 3.82 (s, 3 H).

Provenance & Evidence