methyl 2-bromo-3-(4-fluorophenyl)propanoate

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: Crude methyl 2-bromo-3-(4-fluorophenyl)propionate in acetic acid (330 ml) was stirred and treated with zinc dust (32.75 g) in portions over 30 minutes. The mixture was stirred for an additional 30 minutes and filtered, and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water to give crude methyl 3-(4-fluorophenyl)propionate, which was refluxed with aqueous sodium hydroxide (400 ml, 10%) for 2 hrs, cooled, treated with decolorizing carbon, and filtered. The filtrate was acidified with 5 N HCl and filtered. The filter cake was washed extensively with water to give 3-(4-fluorophenyl)propionic acid (20.0 g) as colourless crystals, mp 90° C. filtered the filter cake was washed with acetic acid After the filtrate was evaporated the residue was partitioned between methylene chloride and water

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

実験手順: A mixture of 4-fluoroaniline (27.75 g), acetone (500 ml) and hydrobromic acid (80 ml, 48%) stirred at -5° C. was treated over 30 minutes with a solution of sodium nitrite (21.0 g) in water (50 ml). Methyl acrylate (215 g) and cuprous bromide (0.04 g) were added. The internal temperature was allowed to rise in a carefully controlled manner; at 15° C. the evolution of N2 was vigorous. When the rate of N2 evolution decreased, the mixture was stirred at 25° C. for 1 hr to complete the reaction. The mixture was evaporated, and the residue was partitioned between water and toluene to give crude methyl 2-bromo-3-(4-fluorophenyl)propionate. at 15° C. the mixture was stirred at 25° C. for 1 hr the reaction The mixture was evaporated the residue was partitioned between water and toluene

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

実験手順: A mixture of 4-fluoroaniline (27.75 g), acetone (500 ml) and hydrobromic acid (80 ml, 48%) stirred at -5° C. was treated over 30 minutes with a solution of sodium nitrite (21.0 g) in water (50 ml). Methyl acrylate (215 g) and cuprous bromide (0.04 g) were added. The internal temperature was allowed to rise in a carefully controlled manner; at 15° C. the evolution of N2 was vigorous. When the rate of N2 evolution decreased, the mixture was stirred at 25° C. for 1 hr to complete the reaction. The mixture was evaporated, and the residue was partitioned between water and toluene to give crude methyl 2-bromo-3-(4-fluorophenyl)propionate. at 15° C. the mixture was stirred at 25° C. for 1 hr the reaction The mixture was evaporated the residue was partitioned between water and toluene

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

実験手順: Crude methyl 2-bromo-3-(4-fluorophenyl)propionate in acetic acid (330 ml) was stirred and treated with zinc dust (32.75 g) in portions over 30 minutes. The mixture was stirred for an additional 30 minutes and filtered, and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water to give crude methyl 3-(4-fluorophenyl)propionate, which was refluxed with aqueous sodium hydroxide (400 ml, 10%) for 2 hrs, cooled, treated with decolorizing carbon, and filtered. The filtrate was acidified with 5 N HCl and filtered. The filter cake was washed extensively with water to give 3-(4-fluorophenyl)propionic acid (20.0 g) as colourless crystals, mp 90° C. filtered the filter cake was washed with acetic acid After the filtrate was evaporated the residue was partitioned between methylene chloride and water

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

実験手順: A mixture of 4-fluoroaniline (27.75 g), acetone (500 ml) and hydrobromic acid (80 ml, 48%) stirred at -5° C. was treated over 30 minutes with a solution of sodium nitrite (21.0 g) in water (50 ml). Methyl acrylate (215 g) and cuprous bromide (0.04 g) were added. The internal temperature was allowed to rise in a carefully controlled manner; at 15° C. the evolution of N2 was vigorous. When the rate of N2 evolution decreased, the mixture was stirred at 25° C. for 1 hr to complete the reaction. The mixture was evaporated, and the residue was partitioned between water and toluene to give crude methyl 2-bromo-3-(4-fluorophenyl)propionate. at 15° C. the mixture was stirred at 25° C. for 1 hr the reaction The mixture was evaporated the residue was partitioned between water and toluene