methyl 2-(3-amino-4-fluorophenyl)acetate

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

実験手順: Isovaleryll chloride (2.93 ml, 2.90 g, 0.024 mol) was added, dropwise, to a chilled (ice-bath) solution of methyl 3-amino-4-fluorophenylacetate (4.00 g, 0.022 mol) in pyridine (16 ml) and, once the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Trituration with dichloromethane/hexane gave methyl 4-fluoro-3-(3-methylbutyramido)phenylacetate (4.88 g) as a pale brown solid. once the addition the cooling bath was removed The mixture was diluted with water extracted with ethyl acetate The organic extract was washed with water dried over anhydrous magnesium sulfate filtered the filtrate was evaporated in vacuo

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

実験手順: Iron powder (8.1 g) was added to a solution of methyl 4-fluoro-3-nitrophenylacetate (27.24 g, 0.128 mol) in a mixture of concentrated hydrochloric acid (1.5 ml), isopropanol (265 ml) and water (26.5 ml) and the mixture was stirred at room temperature for 1 hour. A second portion of iron powder (8.1 g) was added and the mixture was heated to reflux for 1 hour. A further quantity of concentrated hydrochloric acid was added and the mixture was refluxed for a further 1 hour. The mixture was cooled to room temperature, filtered through a plug of Hyflo® diatomaceous earth and the filtrate was evaporated in vacuo to give methyl 3-amino-4-fluorophenylacetate (22.98 g) which was used without further purification in the next step. the mixture was heated to reflux for 1 hour the mixture was refluxed for a further 1 hour The mixture was cooled to room temperature filtered through a plug of Hyflo® diatomaceous earth the filtrate was evaporated in vacuo

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

実験手順: Isovaleryll chloride (2.93 ml, 2.90 g, 0.024 mol) was added, dropwise, to a chilled (ice-bath) solution of methyl 3-amino-4-fluorophenylacetate (4.00 g, 0.022 mol) in pyridine (16 ml) and, once the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Trituration with dichloromethane/hexane gave methyl 4-fluoro-3-(3-methylbutyramido)phenylacetate (4.88 g) as a pale brown solid. once the addition the cooling bath was removed The mixture was diluted with water extracted with ethyl acetate The organic extract was washed with water dried over anhydrous magnesium sulfate filtered the filtrate was evaporated in vacuo

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

実験手順: Iron powder (8.1 g) was added to a solution of methyl 4-fluoro-3-nitrophenylacetate (27.24 g, 0.128 mol) in a mixture of concentrated hydrochloric acid (1.5 ml), isopropanol (265 ml) and water (26.5 ml) and the mixture was stirred at room temperature for 1 hour. A second portion of iron powder (8.1 g) was added and the mixture was heated to reflux for 1 hour. A further quantity of concentrated hydrochloric acid was added and the mixture was refluxed for a further 1 hour. The mixture was cooled to room temperature, filtered through a plug of Hyflo® diatomaceous earth and the filtrate was evaporated in vacuo to give methyl 3-amino-4-fluorophenylacetate (22.98 g) which was used without further purification in the next step. the mixture was heated to reflux for 1 hour the mixture was refluxed for a further 1 hour The mixture was cooled to room temperature filtered through a plug of Hyflo® diatomaceous earth the filtrate was evaporated in vacuo

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

実験手順: Methyl 4-fluoro-3-nitrophenylacetate (5.0 g, 0.023 mol) and iron powder (3 g, 0.053 mol) were suspended in a mixture of propan-2-ol (50 ml) and water (5 ml). Concentrated hydrochloric acid (5 drops) was added at room temperature and the mixture was heated at reflux with stirring for 2 hours. The reaction mixture was cooled, diluted with diethyl ether, filtered through diatomaceous earth and the resulting filtrate was evaporated in vacuo. The residue was further purified by chromatography on silica gel, eluting with diethyl ether to yield methyl 3-amino-4-fluorophenylacetate (3.5 g) as a yellow oil. the mixture was heated at reflux The reaction mixture was cooled filtered through diatomaceous earth the resulting filtrate was evaporated in vacuo The residue was further purified by chromatography on silica gel eluting with diethyl ether

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

実験手順: Isovaleryll chloride (2.93 ml, 2.90 g, 0.024 mol) was added, dropwise, to a chilled (ice-bath) solution of methyl 3-amino-4-fluorophenylacetate (4.00 g, 0.022 mol) in pyridine (16 ml) and, once the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. Trituration with dichloromethane/hexane gave methyl 4-fluoro-3-(3-methylbutyramido)phenylacetate (4.88 g) as a pale brown solid. once the addition the cooling bath was removed The mixture was diluted with water extracted with ethyl acetate The organic extract was washed with water dried over anhydrous magnesium sulfate filtered the filtrate was evaporated in vacuo

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

実験手順: Iron powder (8.1 g) was added to a solution of methyl 4-fluoro-3-nitrophenylacetate (27.24 g, 0.128 mol) in a mixture of concentrated hydrochloric acid (1.5 ml), isopropanol (265 ml) and water (26.5 ml) and the mixture was stirred at room temperature for 1 hour. A second portion of iron powder (8.1 g) was added and the mixture was heated to reflux for 1 hour. A further quantity of concentrated hydrochloric acid was added and the mixture was refluxed for a further 1 hour. The mixture was cooled to room temperature, filtered through a plug of Hyflo® diatomaceous earth and the filtrate was evaporated in vacuo to give methyl 3-amino-4-fluorophenylacetate (22.98 g) which was used without further purification in the next step. the mixture was heated to reflux for 1 hour the mixture was refluxed for a further 1 hour The mixture was cooled to room temperature filtered through a plug of Hyflo® diatomaceous earth the filtrate was evaporated in vacuo