2-(4-fluorophenyl)sulfanylaniline

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Fluorophenyl)sulfanyl]aniline (400 mg, 1.6 mmol) was stirred at 0° C. in conc. HCl (4.0 mL) and NaNO2 (130 mg, 1.8 mmol) was added slowly, maintaining 0° C. reaction temperature. After stirring for 1 hour at 0° C., a solution of SnCl2 (610 mg, 3.2 mmol) in 1.5 mL conc. HCl was added. The reaction was brought to rt and stirred for one h. Upon completion, the reaction was basified with 1N aqueous NaOH to pH 12. The reaction mixture was partition between water and CHCl3 and the aqueous layer extracted with CHCl3 (3×20 mL). The combined extracts were washed with brine (20 mL), H2O (20 mL) and dried (Na2SO4) and evaporated to a residue. The residue was taken up in a minimal amount of CHCl3 (10 mL) and 1N HCl-Ether (10 mL) was added. The solvent was evaporated affording 1-{2-[(4-fluorophenyl)sulfanyl]phenyl}hydrazine hydrochloride as a dark semi-solid (327 mg, 76%). 1H NMR (CD3OD, 300 MHz) δ 7.40-7.51 (m, 2H), 7.16-7.25 (m, 2H), 6.95-7.14 (m, 4H) ppm. reaction temperature was brought to rt stirred for one h The reaction mixture was partition between water and CHCl3 the aqueous layer extracted with CHCl3 (3×20 mL) The combined extracts were washed with brine (20 mL), H2O (20 mL) dried (Na2SO4) evaporated to a residue was added The solvent was evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Fluorophenyl)sulfanyl]aniline (400 mg, 1.6 mmol) was stirred at 0° C. in conc. HCl (4.0 mL) and NaNO2 (130 mg, 1.8 mmol) was added slowly, maintaining 0° C. reaction temperature. After stirring for 1 hour at 0° C., a solution of SnCl2 (610 mg, 3.2 mmol) in 1.5 mL conc. HCl was added. The reaction was brought to rt and stirred for one h. Upon completion, the reaction was basified with 1N aqueous NaOH to pH 12. The reaction mixture was partition between water and CHCl3 and the aqueous layer extracted with CHCl3 (3×20 mL). The combined extracts were washed with brine (20 mL), H2O (20 mL) and dried (Na2SO4) and evaporated to a residue. The residue was taken up in a minimal amount of CHCl3 (10 mL) and 1N HCl-Ether (10 mL) was added. The solvent was evaporated affording 1-{2-[(4-fluorophenyl)sulfanyl]phenyl}hydrazine hydrochloride as a dark semi-solid (327 mg, 76%). 1H NMR (CD3OD, 300 MHz) δ 7.40-7.51 (m, 2H), 7.16-7.25 (m, 2H), 6.95-7.14 (m, 4H) ppm. reaction temperature was brought to rt stirred for one h The reaction mixture was partition between water and CHCl3 the aqueous layer extracted with CHCl3 (3×20 mL) The combined extracts were washed with brine (20 mL), H2O (20 mL) dried (Na2SO4) evaporated to a residue was added The solvent was evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(4-Fluorophenyl)sulfanyl]aniline (400 mg, 1.6 mmol) was stirred at 0° C. in conc. HCl (4.0 mL) and NaNO2 (130 mg, 1.8 mmol) was added slowly, maintaining 0° C. reaction temperature. After stirring for 1 hour at 0° C., a solution of SnCl2 (610 mg, 3.2 mmol) in 1.5 mL conc. HCl was added. The reaction was brought to rt and stirred for one h. Upon completion, the reaction was basified with 1N aqueous NaOH to pH 12. The reaction mixture was partition between water and CHCl3 and the aqueous layer extracted with CHCl3 (3×20 mL). The combined extracts were washed with brine (20 mL), H2O (20 mL) and dried (Na2SO4) and evaporated to a residue. The residue was taken up in a minimal amount of CHCl3 (10 mL) and 1N HCl-Ether (10 mL) was added. The solvent was evaporated affording 1-{2-[(4-fluorophenyl)sulfanyl]phenyl}hydrazine hydrochloride as a dark semi-solid (327 mg, 76%). 1H NMR (CD3OD, 300 MHz) δ 7.40-7.51 (m, 2H), 7.16-7.25 (m, 2H), 6.95-7.14 (m, 4H) ppm. reaction temperature was brought to rt stirred for one h The reaction mixture was partition between water and CHCl3 the aqueous layer extracted with CHCl3 (3×20 mL) The combined extracts were washed with brine (20 mL), H2O (20 mL) dried (Na2SO4) evaporated to a residue was added The solvent was evaporated