Potassium Carbonate → 4-(2,5-Dichlorophenylthio)-3-nitrobenzonitrile

Participants

Reaction Steps

To a solution of 4-chloro-3-nitrobenzonitrile (10.0 g, 54.77 mmol) in THF (300 mL) was added 2,5-dichlorobenzenethiol (19.6 g, 12.108 mmol) and K2CO3 (37.8 g, 273.85 mmol). The reaction mixture was refluxed for 48 hrs. The solid was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated NaHCO3, H2O, and saturated NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo. The resulting solid was then triturated with DCM and hexanes, and filtered to yield compound 27 as a yellow solid (11.823 g, 91.0% HPLC purity, 66.4% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.82 (d, J=2 Hz, 1H), 8.00 (m, 3H), 7.80 (d, J=9 Hz, 1H), 7.75 (dd, J1=3 Hz, J2=9 Hz, 1H), 6.97 (d, J=9 Hz, 2H).

Provenance & Evidence