1-Chloro-2-nitrobenzene → 4-Fluorophenyl 2-nitrophenyl sulfide

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].[H-].[Na+]>C1COCC1>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)([O-:18])=[O:17]

Participants

Procedure

To a solution of 4-fluorothiophenol (1.0 g, 7.8 mmol) and 2-chloronitrobenzene (1.2 g, 7.8 mmol) in THF (10 mL) at 0° C. was added NaH (60% dispersion in oil, 390 mg, 9.4 mmol). The reaction was brought to room temperature and allowed to stir for 18 h. Ice was added and the layers separated. The aqueous layer was extracted three times with EtOAc (3×50 mL). The combined extracts were washed with water (50 mL) and dried (Na2SO4) and evaporated affording 4-fluorophenyl 2-nitrophenyl sulfide (1.6 g, 82%) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.24 (dd, 1H, J=1.5, 8 Hz), 7.58-7.63 (m, 2H), 7.38 (dt, 1H, J=1.5, 7.4 Hz), 7.15-7.25 (m, 3H), 6.82 (dd, 1H, J=1.1, 8.1 Hz) ppm.