Water → 1-(Ethylsulfanyl)-4-nitrobenzene

Participants

Reaction Steps

To a solution of NaOH (0.13 g, 3.2 mmol) in EtOH (10 mL) was added 4-nitrothiophenol (0.50 g, 3.2 mmol) and iodoethane (0.26 mL, 3.2 mmol). After stirring 2 h the reaction mixture was added to water (30 mL) and extracted with Et2O (3×25 mL). The combined extracts were washed with satd NH4Cl (3×25 mL) and brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex 0:100 to 30:70) to yield 1-ethylthio-4-nitrobenzene (0.35 g, 59%) as a yellow crystalline solid. 1H-NMR (CDCl3) δ 8.13 (2H, d, J=8.8), 7.32 (2H, d, J=8.8), 3.06 (2H, q, J=7.3), 1.41 (3H, t, J=7.3). The title compound was prepared from 1-ethylthio-4-nitrobenzene in a manner similar to that described in Example 3A: MS (ESI): 419 (MH+).

Provenance & Evidence