1-bromo-2-chloro-4-ethylsulfanylbenzene

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

Procedure: To a solution of 1-bromo-2-chloro-4-fluorobenzene (24.8 g, 119 mmol) and ethanethiol (10.6 mL, 143 mmol) in N,N-dimethylformamide (150 mL) was added sodium hydride (60% in oil, 6.00 g, 150 mmol) at room temperature by small portions, and the resulting mixture was stirred for 4 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give the title compound (19.4 g, yield 65%) as a colorless oil. washed twice with water and once with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a room temperature solution of 1-bromo-4-fluoro-2-chlorobenzene (1.9 g, 0.97 mmol) in DMSO (10 mL) was added sodium ethanethiolate (0.84 g, 1 mmol) and the resulting reaction mixture was heated to 100° C. for 18 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (3×50 mL). The organic layers were combined and washed with saturated brine solution (20 mL) then dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with heptane to afford the title compound as a colourless liquid in 70% yield, 1.6 g. the resulting reaction mixture The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL) The organic layer was separated the aqueous layer was further extracted with EtOAc (3×50 mL) washed with saturated brine solution (20 mL) then dried over Na2SO4 filtered concentrated in vacuo The crude material was purified by silica gel column chromatography eluting with heptane

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

Procedure: To a solution of 1-bromo-2-chloro-4-fluorobenzene (24.8 g, 119 mmol) and ethanethiol (10.6 mL, 143 mmol) in N,N-dimethylformamide (150 mL) was added sodium hydride (60% in oil, 6.00 g, 150 mmol) at room temperature by small portions, and the resulting mixture was stirred for 4 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give the title compound (19.4 g, yield 65%) as a colorless oil. washed twice with water and once with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane)