3,5-dichloro-4-(2,2,2-trifluoroethoxy)aniline

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

Procedure: 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, 6.15 mmol) in THF (20 mL) was added isopentyl nitrite (2.94 g, 17.22 mmol) dropwise. The resulting solution was refluxed for 6 h and the solvent was removed under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE to provide 1,3-dichloro-2-(2,2,2-trifluoroethoxy)benzene as colorless oil. The resulting solution was refluxed for 6 h the solvent was removed under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, 6.15 mmol) in THF (20 mL) was added isopentyl nitrite (2.94 g, 17.22 mmol) dropwise. The resulting solution was refluxed for 6 h and the solvent was removed under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE to provide 1,3-dichloro-2-(2,2,2-trifluoroethoxy)benzene as colorless oil. The resulting solution was refluxed for 6 h the solvent was removed under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: To a solution of 1,3-dichloro-5-nitro-2-(2,2,2-trifluoroethoxy)benzene (1.90 g, 6.55 mmol) in MeOH (20 mL) and 12 N HCl (20 mL) at rt, SnCl2 (3.72 g, 19.66 mmol) was slowly added to it and then the reaction mixture was stirred overnight at rt. To the reaction mixture was slowly added 3N NaOH to pH=10 and then extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (6:1) to provide 3,5-dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, yield 94%) as pale yellow oil. extracted with EA The combined organic layers were washed with brine dried over anhydrous Na2SO4 concentrated under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, 6.15 mmol) in THF (20 mL) was added isopentyl nitrite (2.94 g, 17.22 mmol) dropwise. The resulting solution was refluxed for 6 h and the solvent was removed under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE to provide 1,3-dichloro-2-(2,2,2-trifluoroethoxy)benzene as colorless oil. The resulting solution was refluxed for 6 h the solvent was removed under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: To a solution of 1,3-dichloro-5-nitro-2-(2,2,2-trifluoroethoxy)benzene (1.90 g, 6.55 mmol) in MeOH (20 mL) and 12 N HCl (20 mL) at rt, SnCl2 (3.72 g, 19.66 mmol) was slowly added to it and then the reaction mixture was stirred overnight at rt. To the reaction mixture was slowly added 3N NaOH to pH=10 and then extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (6:1) to provide 3,5-dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, yield 94%) as pale yellow oil. extracted with EA The combined organic layers were washed with brine dried over anhydrous Na2SO4 concentrated under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, 6.15 mmol) in THF (20 mL) was added isopentyl nitrite (2.94 g, 17.22 mmol) dropwise. The resulting solution was refluxed for 6 h and the solvent was removed under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE to provide 1,3-dichloro-2-(2,2,2-trifluoroethoxy)benzene as colorless oil. The resulting solution was refluxed for 6 h the solvent was removed under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE

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

Procedure: To a solution of 1,3-dichloro-5-nitro-2-(2,2,2-trifluoroethoxy)benzene (1.90 g, 6.55 mmol) in MeOH (20 mL) and 12 N HCl (20 mL) at rt, SnCl2 (3.72 g, 19.66 mmol) was slowly added to it and then the reaction mixture was stirred overnight at rt. To the reaction mixture was slowly added 3N NaOH to pH=10 and then extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (6:1) to provide 3,5-dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, yield 94%) as pale yellow oil. extracted with EA The combined organic layers were washed with brine dried over anhydrous Na2SO4 concentrated under reduced pressure The residue was purified by column chromatography over silica gel eluted with PE