1,2-diethoxy-3-fluorobenzene

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 solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmoL) in acetonitrile (900 mL), a solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmoL) in acetonitrile (1.5 L) was added dropwise under ice cooling and stirred overnight at room temperature. After evaporation of the solvent, ethyl acetate was added to the residue, followed by washing with water. The resultant aqueous layer was re-extracted with ethyl acetate, and the extract was mixed with the previously obtained organic layer. The organic layer was washed with water, saturated saline and water in this order and then dried over anhydrous magnesium sulfate. The resultant solution was concentrated to obtain an oily material. Hexane was added to the oily material, and the crystals deposited were removed by filtration. The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure to give 205.65 g of the captioned compound (yield: 96%). After evaporation of the solvent, ethyl acetate was added to the residue by washing with water The resultant aqueous layer was re-extracted with ethyl acetate the extract was mixed with the previously obtained organic layer The organic layer was washed with water, saturated saline and water in this order dried over anhydrous magnesium sulfate The resultant solution was concentrated to obtain an oily material the crystals deposited were removed by filtration The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure

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

実験手順: To a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmoL) in acetonitrile (900 mL), a solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmoL) in acetonitrile (1.5 L) was added dropwise under ice cooling and stirred overnight at room temperature. After evaporation of the solvent, ethyl acetate was added to the residue, followed by washing with water. The resultant aqueous layer was re-extracted with ethyl acetate, and the extract was mixed with the previously obtained organic layer. The organic layer was washed with water, saturated saline and water in this order and then dried over anhydrous magnesium sulfate. The resultant solution was concentrated to obtain an oily material. Hexane was added to the oily material, and the crystals deposited were removed by filtration. The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure to give 205.65 g of the captioned compound (yield: 96%). After evaporation of the solvent, ethyl acetate was added to the residue by washing with water The resultant aqueous layer was re-extracted with ethyl acetate the extract was mixed with the previously obtained organic layer The organic layer was washed with water, saturated saline and water in this order dried over anhydrous magnesium sulfate The resultant solution was concentrated to obtain an oily material the crystals deposited were removed by filtration The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure

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

実験手順: To a solution of 1,2-diethoxy-3-fluorobenzene (2.28 g, 12.4 mol) and N-(hydroxymethyl)phthalimide (2.41 g, 13.6 mol) in 1,2-dimethoxyethane (8 mL), a solution of sulfuric acid (8 mL) in 1,2-dimethoxyethane (8 mL) was added dropwise on ice, and the mixture was stirred at room temperature for twelve hours. The reaction mixture was poured into water (100 mL), and crystals were filtered. The obtained crystals were recrystallized from acetone and water, and the precipitated crystals were filtered. After the filtrate was concentrated under reduced pressure, the residue was crystallized from acetone to give 0.96 g of the title compound (yield: 23%) as white crystals. were filtered The obtained crystals were recrystallized from acetone and water the precipitated crystals were filtered After the filtrate was concentrated under reduced pressure the residue was crystallized from acetone

反応条件: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 500 ml flask were added 38.4 (0.3 mol) of 3-fluorocatechol [H], 12 g (0.3 mol) of sodium hydroxide and 100 ml of ethanol. After cooling to around 10° C., 100 ml of an ethanol solution of 76.3 g (0.7 mol) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 5 hours. After the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 45.5 g of 1,2-diethoxy-3-fluorobenzene [G1] as an oily product. The process yield was 81%. After the termination of the addition, they were reacted under a reflux temperature for 5 hours was added followed by extraction The extraction liquid was washed with water dried the solvent was removed by distillation

反応条件: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 250 ml reactor were added 12.5 (0.08 mol) of 2-ethoxy-3-fluorophenol [F1], 3.2 g (0.08 mol) of sodium hydroxide and 20 ml of ethanol. After cooling to around 10° C., 20 ml of an ethanol solution of 9.6 g (0.088 ml) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 3 hours and, after the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 11.0 g of an oily product [G1]. The process yield was 75%. After the termination of the addition, they were reacted under a reflux temperature for 3 hours was added followed by extraction The extraction liquid was washed with water dried the solvent was removed by distillation

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

実験手順: To a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmoL) in acetonitrile (900 mL), a solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmoL) in acetonitrile (1.5 L) was added dropwise under ice cooling and stirred overnight at room temperature. After evaporation of the solvent, ethyl acetate was added to the residue, followed by washing with water. The resultant aqueous layer was re-extracted with ethyl acetate, and the extract was mixed with the previously obtained organic layer. The organic layer was washed with water, saturated saline and water in this order and then dried over anhydrous magnesium sulfate. The resultant solution was concentrated to obtain an oily material. Hexane was added to the oily material, and the crystals deposited were removed by filtration. The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure to give 205.65 g of the captioned compound (yield: 96%). After evaporation of the solvent, ethyl acetate was added to the residue by washing with water The resultant aqueous layer was re-extracted with ethyl acetate the extract was mixed with the previously obtained organic layer The organic layer was washed with water, saturated saline and water in this order dried over anhydrous magnesium sulfate The resultant solution was concentrated to obtain an oily material the crystals deposited were removed by filtration The solution was re-concentrated to obtain an oily material, which was distilled under reduced pressure

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 N-bromosuccinimide (NBS) (153.72 g, 864 mmol) in acetonitrile (1.5 L) was added dropwise to a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmol) in acetonitrile (900 mL) on ice, and this was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate was added to the residue and washed with water. The obtained aqueous layer was extracted again with ethyl acetate, and the extract was combined with the aforementioned organic layer. The organic layer was washed sequentially with water, saturated brine, and water again, and was dried over anhydrous magnesium sulfate. The solution was concentrated and an oily substance was obtained. Following hexane addition to the oily substance, crystals that have precipitated were removed by filtration. The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure to obtain 205.65 g of the subject compound (yield: 96%). After the solvent was distilled off ethyl acetate was added to the residue washed with water The obtained aqueous layer was extracted again with ethyl acetate The organic layer was washed sequentially with water, saturated brine, and water again was dried over anhydrous magnesium sulfate The solution was concentrated an oily substance was obtained have precipitated were removed by filtration The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure

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

実験手順: A solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmol) in acetonitrile (1.5 L) was added dropwise to a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmol) in acetonitrile (900 mL) on ice, and this was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate was added to the residue and washed with water. The obtained aqueous layer was extracted again with ethyl acetate, and the extract was combined with the aforementioned organic layer. The organic layer was washed sequentially with water, saturated brine, and water again, and was dried over anhydrous magnesium sulfate. The solution was concentrated and an oily substance was obtained. Following hexane addition to the oily substance, crystals that have precipitated were removed by filtration. The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure to obtain 205.65 g of the subject compound (yield: 96%). After the solvent was distilled off ethyl acetate was added to the residue washed with water The obtained aqueous layer was extracted again with ethyl acetate The organic layer was washed sequentially with water, saturated brine, and water again was dried over anhydrous magnesium sulfate The solution was concentrated an oily substance was obtained have precipitated were removed by filtration The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure

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

実験手順: A solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmol) in acetonitrile (1.5 L) was added dropwise to a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmol) in acetonitrile (900 mL) on ice, and this was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate was added to the residue and washed with water. The obtained aqueous layer was extracted again with ethyl acetate, and the extract was combined with the aforementioned organic layer. The organic layer was washed sequentially with water, saturated brine, and water again, and was dried over anhydrous magnesium sulfate. The solution was concentrated and an oily substance was obtained. Following hexane addition to the oily substance, crystals that have precipitated were removed by filtration. The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure to obtain 205.65 g of the subject compound (yield: 96%). After the solvent was distilled off ethyl acetate was added to the residue washed with water The obtained aqueous layer was extracted again with ethyl acetate The organic layer was washed sequentially with water, saturated brine, and water again was dried over anhydrous magnesium sulfate The solution was concentrated an oily substance was obtained have precipitated were removed by filtration The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure

反応条件: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 500 ml flask were added 38.4 (0.3 mol) of 3-fluorocatechol [H], 12 g (0.3 mol) of sodium hydroxide and 100 ml of ethanol. After cooling to around 10° C., 100 ml of an ethanol solution of 76.3 g (0.7 mol) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 5 hours. After the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 45.5 g of 1,2 -diethoxy-3-fluorobenzene [G1] as an oily product. The process yield was 81%. After the termination of the addition, they were reacted under a reflux temperature for 5 hours was added followed by extraction The extraction liquid was washed with water dried the solvent was removed by distillation