5-bromo-2-chloroaniline

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: 90 g of 5-bromo-2-chloronitrobenzene were hydrogenated in 500 ml of methanol at room temperature and under normal pressure with Raney-Nickel as catalyst and hydrogen. Colorless crystals, melting point: 47° C.

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

実験手順: 90 g of 5-bromo-2-chloronitrobenzene were hydrogenated in 500 ml of methanol at room temperature and under normal pressure with Raney-Nickel as catalyst and hydrogen. Colorless crystals, melting point: 47° C.

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: To a stirring solution of 5-Bromo-2-chloroaniline (100 mg, 0.48 mmol) in DCM (5 ml) is added benzenesulfonyl chloride (280 mg, 202 ul, 1.58 mmol) and pyridine (195 ul, 2.42 mmol). The reaction mixture is stirred at room temperature for 18 hours. EtOAc (20 ml) is added and the reaction mixture is washed with 0.1 m HCl (20 ml), the phases are separated and the organic portion is washed with water (3×), dried over MgSO4, concentrated in vacuo and dried in a vacuum oven to afford the title compound. the reaction mixture is washed with 0.1 m HCl (20 ml) the phases are separated the organic portion is washed with water (3×) dried over MgSO4 concentrated in vacuo dried in a vacuum oven

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

実験手順: To a stirring solution of 5-Bromo-2-chloroaniline (100 mg, 0.48 mmol) in DCM (5 ml) is added benzenesulfonyl chloride (280 mg, 202 ul, 1.58 mmol) and pyridine (195 ul, 2.42 mmol). The reaction mixture is stirred at room temperature for 18 hours. EtOAc (20 ml) is added and the reaction mixture is washed with 0.1 m HCl (20 ml), the phases are separated and the organic portion is washed with water (3×), dried over MgSO4, concentrated in vacuo and dried in a vacuum oven to afford the title compound. the reaction mixture is washed with 0.1 m HCl (20 ml) the phases are separated the organic portion is washed with water (3×) dried over MgSO4 concentrated in vacuo dried in a vacuum oven

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 5-bromo-2-chloroaniline (23 g, 0.11 mol) in concentrated hydrochloric acid (150 mL) and water (90 mL) was cooled in an ice/salt bath. A solution of sodium nitrite (8 g, 0.11 mol) in water (50 mL) was added dropwise to the reaction mixture while maintaining the temperature below 4° C. After stirring for 30 minutes the suspension was transferred via cannula to a solution of SnCl2 dihydrate in concentrated hydrochloric acid (170 mL) and cooled to 5° C. The resulting thick suspension was stirred for 2 h at 5° C. and the solid was isolated via filtration. The solid was air dried and then further dried by adding chlorobutane (500 mL) and refluxing using a Dean-Stark condenser. After cooling, the solid was isolated by filtration to afford the title compound as an off-white solid (35.3 g). was cooled in an ice/salt bath while maintaining the temperature below 4° C The resulting thick suspension was stirred for 2 h at 5° C. the solid was isolated via filtration dried further dried by adding chlorobutane (500 mL) refluxing After cooling the solid was isolated by filtration

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

実験手順: 2-Chloro-5-bromoaniline (258 g) is added to concentrated hydrochloric acid (750 ml) and the mixture is stirred at 80°-90° C. until formation of a homogeneous suspension. Then, it is cooled and diazotized at 0°-5° C. by dropwise addition of sodium nitrite (95.1 g) in water (330 ml) during 1 hour. The mixture is stirred for an additional 20 minutes and then a solution of fluoroboric acid (700 ml) (prepared by dissolving 264 g of boric acid in 744 ml of 40% hydrofluoric acid) is added. After 30 minutes of stirring, the separated fluoroborate was filtered, washed successively with a small amount of a fluoroboric acid solution, ethanol and ether, and dried thoroughly in air and in vacuo. The thermal decomposition of the fluoroborate is carried out in two portions. Each portion is heated in a flask with a direct flame, the internal temperature during the decomposition being 130°-170° C. The distillates are combined and shaken with water (250 ml) and ether (250 ml). The ethereal layer is washed with 10% sodium hydroxide solution, 3 N-HCl and water and dried over sodium sulfate. The ether is evaporated and the residue is distilled, yielding 184.2 g (70%) of 2-chloro-5-bromofluorobenzene, b.p. 130°-142° C./20 Torr. Then, it is cooled The mixture is stirred for an additional 20 minutes After 30 minutes of stirring the separated fluoroborate was filtered washed successively with a small amount of a fluoroboric acid solution, ethanol and ether dried thoroughly in air and in vacuo Each portion is heated in a flask with a direct flame being 130°-170° C shaken with water (250 ml) and ether (250 ml) The ethereal layer is washed with 10% sodium hydroxide solution, 3 N-HCl and water dried over sodium sulfate The ether is evaporated the residue is distilled

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

実験手順: 90 g of 5-bromo-2-chloronitrobenzene were hydrogenated in 500 ml of methanol at room temperature and under normal pressure with Raney-Nickel as catalyst and hydrogen. Colorless crystals, melting point: 47° C.

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 5-bromo-2-chloroaniline (23 g, 0.11 mol) in concentrated hydrochloric acid (150 mL) and water (90 mL) was cooled in an ice/salt bath. A solution of sodium nitrite (8 g, 0.11 mol) in water (50 mL) was added dropwise to the reaction mixture while maintaining the temperature below 4° C. After stirring for 30 minutes the suspension was transferred via cannula to a solution of SnCl2 dihydrate in concentrated hydrochloric acid (170 mL) and cooled to 5° C. The resulting thick suspension was stirred for 2 h at 5° C. and the solid was isolated via filtration. The solid was air dried and then further dried by adding chlorobutane (500 mL) and refluxing using a Dean-Stark condenser. After cooling, the solid was isolated by filtration to afford the title compound as an off-white solid (35.3 g). 1H NMR (CD3COCD3): δ 10.25 (br s, 1H), 8.32 (br s, 2H) 7.38 (d, 1H), 7.30 (d, 1H), 7.16 (dd, 1H). was cooled in an ice/salt bath while maintaining the temperature below 4° C The resulting thick suspension was stirred for 2 h at 5° C. the solid was isolated via filtration dried further dried by adding chlorobutane (500 mL) refluxing After cooling the solid was isolated by filtration