4-chloro-2-(4-fluorophenoxy)aniline

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-2-(4-fluorophenoxy)-1-nitrobenzene (4.56 g, 17.0 mmol) and iron powder (3.07 g, 55.0 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature, and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound (3.62 g, 90%). The obtained compound was used for the subsequent reaction without further purification. After the reaction the reaction mixture was cooled to room temperature After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-2-(4-fluorophenoxy)-1-nitrobenzene (4.56 g, 17.0 mmol) and iron powder (3.07 g, 55.0 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature, and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound (3.62 g, 90%). The obtained compound was used for the subsequent reaction without further purification. After the reaction the reaction mixture was cooled to room temperature After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-2-(4-fluorophenoxy)-1-nitrobenzene (4.56 g, 17.0 mmol) and iron powder (3.07 g, 55.0 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature, and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound (3.62 g, 90%). The obtained compound was used for the subsequent reaction without further purification. After the reaction the reaction mixture was cooled to room temperature After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate The solvent was distilled off under reduced pressure