1,1,2,2-tetrafluoro-3-iodopropane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: The title compound is prepared in 89% yield (7.97 g, pale yellow solid) from 6-chloro-4-methylpyridin-3-ol (5.00 g, 34.8 mmol) and 1,1,2,2-tetrafluoro-3-iodopropane (16.9 g, 69.7 mmol) in a similar manner to Step-1 of Amine-49.

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. of dimethylformamide is treated under nitrogen with 0.97 g. of sodium borohydride in 10 ml. of dimethylformamide at 20°-30° C. After 1 hour at 20°-25° C, 6 g. of 2,2,3,3-tetrafluoro-1-iodopropane is added and the mixture is heated at 100° C for 4 hours. The mixture is cooled, diluted with water and extracted with chloroform. Evaporation of the dried chloroform solution yields 2-nitro-4-(2,2,3,3-tetrafluoropropylthio)aniline as an oil. Acetylation of the latter compound in acetic anhydride with sulfuric acid catalysis according to the first paragraph of Example XXI yields 1-acetamido-2-nitro-4-(2,2,3,3-tetrafluoropropylthio)benzene which can be isolated by extraction into chloroform. Alternatively, this may be prepared by substituting 1-acetamido-2-nitro-4-thiocyanatobenzene in the above alkylation reaction. at 20°-30° C The mixture is cooled extracted with chloroform Evaporation of the dried chloroform solution

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. of dimethylformamide is treated under nitrogen with 0.97 g. of sodium borohydride in 10 ml. of dimethylformamide at 20°-30° C. After 1 hour at 20°-25° C, 6 g. of 2,2,3,3-tetrafluoro-1-iodopropane is added and the mixture is heated at 100° C for 4 hours. The mixture is cooled, diluted with water and extracted with chloroform. Evaporation of the dried chloroform solution yields 2-nitro-4-(2,2,3,3-tetrafluoropropylthio)aniline as an oil. Acetylation of the latter compound in acetic anhydride with sulfuric acid catalysis according to the first paragraph of Example XXI yields 1-acetamido-2-nitro-4-(2,2,3,3-tetrafluoropropylthio)benzene which can be isolated by extraction into chloroform. Alternatively, this may be prepared by substituting 1-acetamido-2-nitro-4-thiocyanatobenzene in the above alkylation reaction. at 20°-30° C The mixture is cooled extracted with chloroform Evaporation of the dried chloroform solution

反応条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-nitro phenol (860 mg, 6.1 mmol) in DMF (10 ml) was added potassium carbonate (1.4 g, 10 mmol) and 1,1,2,2-tetrafluoro-3-iodo-propane (500 mg, 2 mmol). The reaction mixture was heated at 100-110° C. for 6 hr, then cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (100 ml), then washed once with 5% sodium hydroxide solution, several times with water, and finally brine. The organic layer was then dried over anhydrous sodium sulfate, filtered, and evaporated to dryness to give 1-nitro-4-(2,2,3,3-tetrafluoro-propoxy)-benzene (360 mg, 68%) as solid. cooled to room temperature filtered The filtrate was diluted with ethyl acetate (100 ml) washed once with 5% sodium hydroxide solution, several times with water, and finally brine The organic layer was then dried over anhydrous sodium sulfate filtered evaporated to dryness

反応条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-nitro phenol (860 mg, 6.1 mmol) in DMF (10 ml) was added potassium carbonate (1.4 g, 10 mmol) and 1,1,2,2-tetrafluoro-3-iodo-propane (500 mg, 2 mmol). The reaction mixture was heated at 100-110° C. for 6 hr, then cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (100 ml), then washed once with 5% sodium hydroxide solution, several times with water, and finally brine. The organic layer was then dried over anhydrous sodium sulfate, filtered, and evaporated to dryness to give 1-nitro-4-(2,2,3,3-tetrafluoro-propoxy)-benzene (360 mg, 68%) as solid. cooled to room temperature filtered The filtrate was diluted with ethyl acetate (100 ml) washed once with 5% sodium hydroxide solution, several times with water, and finally brine The organic layer was then dried over anhydrous sodium sulfate filtered evaporated to dryness

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

実験手順: 1,1,2,2-Tetrafluoro-3-iodo propane (0.5 g, 2 mmol) was added to a mixture of 5-nitro-2-hydroxy pyridine (860 mg, 6.1 mmol) and potassium carbonate (1.4 g, 10 mmol) in DMF (10 ml) and the reaction heated at reflux for 6 hr. The reaction mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (50 ml), washed successively with bicarbonate solution, water, brine, and dried. Concentration to dryness yielded 5-nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine (394 mg, 75%) as an oil. the reaction heated at reflux for 6 hr filtered The filtrate was diluted with ethyl acetate (50 ml) washed successively with bicarbonate solution, water, brine dried Concentration to dryness

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir: