4-bromo-2-fluoro-5-methoxyaniline

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

実験手順: 4-Bromo-2-fluoro-5-methoxyaniline (1.1 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.8 g) were dissolved in acetic acid (5 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 0.6 g of N-(4-bromo-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 12). M.P., 105°-106° C. refluxed for 3 hours followed by extraction with ether The ether extract was washed with water dried over anhydrous sodium sulfate subjected to filtration The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography

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

実験手順: 4-Bromo-2-fluoro-5-methoxyaniline (1.1 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.8 g) were dissolved in acetic acid (5 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 0.6 g of N-(4-bromo-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 12). M.P., 105°-106° C. refluxed for 3 hours followed by extraction with ether The ether extract was washed with water dried over anhydrous sodium sulfate subjected to filtration The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography

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

実験手順: To a stirred solution of 30.0 g (0.12 mole) of 4-bromo-2-fluoro-5-methoxynitrobenzene in 200 mL of acetic acid was added 40 mL of water, followed by the portionwise addition of 30.0 g (0.54 mole) of iron filings during a 2.5 hour period. Upon complete addition, the reaction mixture was stirred at 25°-35° C. for one hour. Diethyl ether, 200 mL, was added, and the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was washed with 200 mL of water. The organic layer was separated and neutralized with solid sodium bicarbonate. The mixture was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from petroleum ether to give 23.5 g of 4-bromo-2-fluoro-5-methoxyaniline; m.p. 60°-62° C. Upon complete addition the reaction mixture was filtered through a pad of diatomaceous earth The filtrate was washed with 200 mL of water The organic layer was separated The mixture was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a residual solid The solid was recrystallized from petroleum ether

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

実験手順: To a stirred solution of 30.0 g (0.12 mole) of 4-bromo-2-fluoro-5-methoxynitrobenzene in 200 mL of acetic acid was added 40 mL of water, followed by the portionwise addition of 30.0 g (0.54 mole) of iron filings during a 2.5 hour period. Upon complete addition, the reaction mixture was stirred at 25°-35° C. for one hour. Diethyl ether, 200 mL, was added, and the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was washed with 200 mL of water. The organic layer was separated and neutralized with solid sodium bicarbonate. The mixture was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from petroleum ether to give 23.5 g of 4-bromo-2-fluoro-5-methoxyaniline; m.p. 60°-62° C. Upon complete addition the reaction mixture was filtered through a pad of diatomaceous earth The filtrate was washed with 200 mL of water The organic layer was separated The mixture was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a residual solid The solid was recrystallized from petroleum ether

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

実験手順: 4-Bromo-2-fluoro-5-methoxyaniline (1.1 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.8 g) were dissolved in acetic acid (5 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 0.6 g of N-(4-bromo-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 12). refluxed for 3 hours followed by extraction with ether The ether extract was washed with water dried over anhydrous sodium sulfate subjected to filtration The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography

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

実験手順: 4-Bromo-2-fluoro-5-methoxyaniline (1.1 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.8 g) were dissolved in acetic acid (5 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 0.6 g of N-(4-bromo-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 12). M.P., 105°-106° C. refluxed for 3 hours followed by extraction with ether The ether extract was washed with water dried over anhydrous sodium sulfate subjected to filtration The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography

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

実験手順: 4-Bromo-2-fluoro-5-methoxyaniline (1.1 g) and 3,4,5,6-tetrahydrophthalic anhydride (0.8 g) were dissolved in acetic acid (5 ml) and refluxed for 3 hours. The resultant mixture was allowed to cool to room temperature and poured into water, followed by extraction with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography to obtain 0.6 g of N-(4-bromo-2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimide (Compound No. 12). M.P., 105°-106° C. refluxed for 3 hours followed by extraction with ether The ether extract was washed with water dried over anhydrous sodium sulfate subjected to filtration The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography

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

実験手順: To a stirred solution of 30.0 g (0.12 mole) of 4-bromo-2-fluoro-5-methoxynitrobenzene in 200 mL of acetic acid was added 40 mL of water, followed by the portionwise addition of 30.0 g (0.54 mole) of iron filings during a 2.5 hour period. Upon complete addition, the reaction mixture was stirred at 25°-35° C. for one hour. Diethyl ether, 200 mL, was added, and the reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was washed with 200 mL of water. The organic layer was separated and neutralized with solid sodium bicarbonate. The mixture was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from petroleum ether to give 23.5 g of 4-bromo-2-fluoro-5-methoxyaniline; m.p. 60°-62° C. Upon complete addition the reaction mixture was filtered through a pad of diatomaceous earth The filtrate was washed with 200 mL of water The organic layer was separated The mixture was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure to give a residual solid The solid was recrystallized from petroleum ether