methyl 2-(trifluoromethoxy)benzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 min keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a three-necked round bottom flask, equipped with a thermometer and a separatory funnel, HNO3 (5 mL fuming, 100%) was cooled in an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added to the cooled HNO3 within 0.5 hour while keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was added to ice water and an oil separated. The oily residue was added water (50 mL), neutralised with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. was cooled in an ice bath the temperature below 15° C an oil separated The oily residue was added water (50 mL) extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 min keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. 1H NMR (DMSO-d6): δ 3.93 (3H, s), 7.82 (1H, d), 8.58 (1H, d), 8.67 (1H, s); HPLC-MS (method B): m/z: 266; Rt=6.0 min. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a three-necked round bottom flask, equipped with a thermometer and a separatory funnel, HNO3 (5 mL fuming, 100%) was cooled in an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added to the cooled HNO3 within 0.5 hour while keeping the temperature below 15° C. The reacti0n was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was added to ice water and an oil separated. The oily residue was added water (50 mL), neutralised with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. was cooled in an ice bath the temperature below 15° C an oil separated The oily residue was added water (50 mL) extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 min keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 min keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a three-necked round bottom flask, equipped with a thermometer and a separatory funnel, HNO3 (5 mL fuming, 100%) was cooled in an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added to the cooled HNO3 within 0.5 hour while keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was added to ice water and an oil separated. The oily residue was added water (50 mL), neutralised with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. was cooled in an ice bath the temperature below 15° C an oil separated The oily residue was added water (50 mL) extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a three-necked round bottom flask, equipped with a thermometer and a separatory funnel, HNO3 (5 mL fuming, 100%) was cooled in an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added to the cooled HNO3 within 0.5 hour while keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was added to ice water and an oil separated. The oily residue was added water (50 mL), neutralised with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. was cooled in an ice bath the temperature below 15° C an oil separated The oily residue was added water (50 mL) extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 minutes keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (MgSO4), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (MgSO4) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 minutes keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (MgSO4), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (MgSO4) concentrated in vacuo

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fuming nitric acid (5 mL) was cooled on an ice bath. Methyl 2-(trifluoromethoxy)benzoate (5 g, 22.7 mmol) was slowly added within 30 min keeping the temperature below 15° C. The reaction was then stirred at 60° C. for 1 hour and 2 hours at room temperature. The mixture was poured on ice water whereupon an oil separated. The aqueous supernatant was decanted and additional water (50 mL) was added to the oil. After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL). The aqueous phase was extracted with ethyl acetate (15 mL) once more. The combined organic phases were washed with saturated sodium chloride (2×15 mL), dried (magnesium sulphate), and concentrated in vacuo to give 5.69 g of 5-nitro-2-trifluoromethoxybenzoic acid methyl ester. 1H NMR (DMSO-d6): δ 3.93 (3H, s), 7.82 (1H, d), 8.58 (1H, d), 8.67 (1H, s); HPLC-MS (method B): m/z: 266; Rt=6.0 min. the temperature below 15° C The mixture was poured on ice water whereupon an oil separated The aqueous supernatant was decanted additional water (50 mL) was added to the oil After neutralisation with sodium hydrogen carbonate, the mixture was extracted with ethyl acetate (25 mL) The aqueous phase was extracted with ethyl acetate (15 mL) once more The combined organic phases were washed with saturated sodium chloride (2×15 mL) dried (magnesium sulphate) concentrated in vacuo