N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide

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: A solution of 4-fluoro-2-(trifluoromethyl)aniline (5.0 g, 27.91 mmol) in acetic anhydride (25 mL) was stirred at ambient temperature for 3 hours to produce a white needle precipitate. The reaction mixture was poured onto ice water, filtered then dried to give 6.0 g of N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide as an off-white solid which was used without further purification. The N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (2.0 g, 9.04 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to 0 degrees Centigrade using an ice bath. 70% HNO3 (1.5 mL) was added drop wise and the reaction stirred at 0 degrees Centigrade for 30 min and then at ambient temperature for 3 hours. The reaction mixture was poured onto ice-water, filtered then dried to give 2.4 g of the desired N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide. to produce a white needle precipitate The reaction mixture was poured onto ice water filtered then dried

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

実験手順: A solution of 4-fluoro-2-(trifluoromethyl)aniline (5.0 g, 27.91 mmol) in acetic anhydride (25 mL) was stirred at ambient temperature for 3 hours to produce a white needle precipitate. The reaction mixture was poured onto ice water, filtered then dried to give 6.0 g of N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide as an off-white solid which was used without further purification. The N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (2.0 g, 9.04 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to 0 degrees Centigrade using an ice bath. 70% HNO3 (1.5 mL) was added drop wise and the reaction stirred at 0 degrees Centigrade for 30 min and then at ambient temperature for 3 hours. The reaction mixture was poured onto ice-water, filtered then dried to give 2.4 g of the desired N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide. was used without further purification cooled to 0 degrees Centigrade at ambient temperature for 3 hours The reaction mixture was poured onto ice-water filtered then dried

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-acetamido-5-fluorobenzotrifluoride (1.369 g, 6.19 mmol) in concentrated H2SO4 (6 mL) at 0° C. was added dropwise 70% HNO3 (0.8 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (25 g). The precipitate was collected by filtration, affording 2.1 g of crude 2-acetamido-5-fluoro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to afford 1.50 g of pure compound as yellow needles. at room temperature for 3 h The precipitate was collected by filtration

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-acetamido-5-fluorobenzotrifluoride (1.369 g, 6.19 mmol) in concentrated H2SO4 (6 mL) at 0° C. was added dropwise 70% HNO3 (0.8 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (25 g). The precipitate was collected by filtration, affording 2.1 g of crude 2-acetamido-5-fluoro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to afford 1.50 g of pure compound as yellow needles. at room temperature for 3 h The precipitate was collected by filtration

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

実験手順: A solution of 2-amino-5-fluorobenzotrifluoride (2.025 g, 11.31 mmol, Aldrich) in acetic anhydride (10 mL) was stirred at room temperature for 12 h, and then most of the acetic anhydride was removed. The white needle crystals were collected by filtration, affording 2.445 g (98%) of 2-acetamido-5-fluorobenzotrifluoride. 1H NMR (CDCl3): δ2.205 (s, 3H); 7.229-7.335 (m, 3H); 8.055 (dd, 1H, J1 =4.8 Hz, J2 =8.4 Hz). most of the acetic anhydride was removed The white needle crystals were collected by filtration

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-acetamido-5-fluorobenzotrifluoride (1.369 g, 6.19 mmol) in concentrated H2SO4 (6 mL) at 0° C. was added dropwise 70% HNO3 (0.8 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (25 g). The precipitate was collected by filtration, affording 2.1 g of crude 2-acetamido-5-fluoro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to afford 1.50 g of pure compound as yellow needles. at room temperature for 3 h The precipitate was collected by filtration

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

実験手順: A solution of 2-amino-5-fluorobenzotrifluoride (2.025 g, 11.31 mmol, Aldrich) in acetic anhydride (10 mL) was stirred at room temperature for 12 h, and then most of the acetic anhydride was removed. The white needle crystals were collected by filtration, affording 2.445 g (98%) of 2-acetamido-5-fluorobenzotrifluoride. 1H NMR (CDCl3): δ2.205 (s, 3H); 7.229-7.335 (m, 3H); 8.055 (dd, 1H, J1 =4.8 Hz, J2 =8.4 Hz). most of the acetic anhydride was removed The white needle crystals were collected by filtration

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2-acetamido-5-fluorobenzotrifluoride (1.369 g, 6.19 mmol) in concentrated H2SO4 (6 mL) at 0° C. was added dropwise 70% HNO3 (0.8 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (25 g). The precipitate was collected by filtration, affording 2.1 g of crude 2-acetamido-5-fluoro-3-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to afford 1.50 g of pure compound as yellow needles. at room temperature for 3 h The precipitate was collected by filtration

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

実験手順: A solution of 2-amino-5-fluorobenzotrifluoride (2.025 g, 11.31 mmol, Aldrich) in acetic anhydride (10 mL) was stirred at room temperature for 12 h, and then most of the acetic anhydride was removed. The white needle crystals were collected by filtration, affording 2.445 g (98%) of 2-acetamido-5-fluorobenzotrifluoride. 1H NMR (CDCl3): δ 2.205 (S, 3H); 7.229-7.335 (m, 3H); 8.055 (dd, 1H, J1 =4.8 Hz, J2 =8.4 Hz). most of the acetic anhydride was removed The white needle crystals were collected by filtration

反応条件: temp:0.00; pressure:0.00; stir: