5-chloro-2-(2,2,2-trifluoroethoxy)benzonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser were placed 400 mg (1.7 mmol) of the above nitrile and 10 ml of formic acid. To the system were added ca. 500 mg of Raney nickel and the mixture was heated at ref lux for 6 hours and stirred at room temperature overnight. The mixture was filtered through a pad of a diatomaceous earth, and the pad was rinsed with water and CHCl3. The layers were separated and the aqueous phase was extracted with three portions of CHCl3. The combined organic fractions were dried and concentrated to obtain 270 mg of the title compound. Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser the mixture was heated at ref lux for 6 hours The mixture was filtered through a pad of a diatomaceous earth the pad was rinsed with water and CHCl3 The layers were separated the aqueous phase was extracted with three portions of CHCl3 The combined organic fractions were dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser were placed 400 mg (1.7 mmol) of the above nitrile and 10 ml of formic acid. To the system were added ca. 500 mg of Raney nickel and the mixture was heated at ref lux for 6 hours and stirred at room temperature overnight. The mixture was filtered through a pad of a diatomaceous earth, and the pad was rinsed with water and CHCl3. The layers were separated and the aqueous phase was extracted with three portions of CHCl3. The combined organic fractions were dried and concentrated to obtain 270 mg of the title compound. Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser the mixture was heated at ref lux for 6 hours The mixture was filtered through a pad of a diatomaceous earth the pad was rinsed with water and CHCl3 The layers were separated the aqueous phase was extracted with three portions of CHCl3 The combined organic fractions were dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere, in a round-bottom flask equipped with a refluxcondenser were placed 400 mg (1.7 mmol) of the above nitrile and 10 ml of formic acid. To the system were added ca. 500 mg of Raney nickel and the mixture was heated at reflux for 6 hours and stirred at room temperature overnight. The mixture was filtered through a pad of a diatomaceous earth,and the pad was rinsed with water and CHCl3. The layers were separatedand the aqueous phase was extracted with three portions of CHCl3. The combined organic fractions were dried and concentrated to obtain 270 mg ofthe title compound. Under a nitrogen atmosphere, in a round-bottom flask equipped with a refluxcondenser the mixture was heated at reflux for 6 hours The mixture was filtered through a pad of a diatomaceous earth,and the pad was rinsed with water and CHCl3 was extracted with three portions of CHCl3 The combined organic fractions were dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere, in a round-bottom flask were placed 880 mg (22mmol) of 60% sodium hydride (NaH) and 12 ml of N,N-dimethylformamide. To the system were added 2.9 ml (4 g, 40 mmol) of 2,2,2-trifluoroethanol via syringe over a period of 15 minutes and the mixture was stirred at room temperature for 20 minutes. To the system were added 1.72 g (10 mmol) of 2,5-dichlorobenzonitrile, and the mixture was heated at 90° C. for three days. The mixture was cooled to room temperature, poured into 50 ml of 2M aqueous HCl and extracted with three portions of ether. The combinedorganic fractions were dried (Na2SO4) and concentrated to afford2.5 g of a solid. The crude material was purified by flash column chromatography using 1:49 ethyl acetate/hexanes as the eluant to obtain 1.4 g of 5-chloro-2-(2,2,2-trifluoroethoxy)benzonitrile as a white solid. Under a nitrogen atmosphere, in a round-bottom flask were placed the mixture was heated at 90° C. for three days The mixture was cooled to room temperature extracted with three portions of ether The combinedorganic fractions were dried (Na2SO4) concentrated to afford2 The crude material was purified by flash column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser were placed 400 mg (1.7 mmol) of the above nitrile and 10 ml of formic acid. To the system were added ca. 500 mg of Raney nickel and the mixture was heated at ref lux for 6 hours and stirred at room temperature overnight. The mixture was filtered through a pad of a diatomaceous earth, and the pad was rinsed with water and CHCl3. The layers were separated and the aqueous phase was extracted with three portions of CHCl3. The combined organic fractions were dried and concentrated to obtain 270 mg of the title compound. Under a nitrogen atmosphere, in a round-bottom flask equipped with a reflux condenser the mixture was heated at ref lux for 6 hours The mixture was filtered through a pad of a diatomaceous earth the pad was rinsed with water and CHCl3 The layers were separated the aqueous phase was extracted with three portions of CHCl3 The combined organic fractions were dried concentrated