3-(2,4-dichloro-5-fluorophenyl)-3-oxopropanenitrile

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 21 g of 2,4-dichloro-5-fluoro-benzoyl-acetonitrile, 19.2 g of methyl o-formate and 23.1 g of acetic anhydride is refluxed at a bath temperature of 150° C. for 3 hours. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C. 24.5 g (99%) of 2-(2,4-dichloro-5-fluorobenzoyl)3-methoxy-acrylonitrile are obtained. A sample recrystallized from toluene gives colorless crystals of melting point 159° C. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C

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

実験手順: 23.2 g (0.1 mole) of 5-(2,4-dichloro-5-fluoro- phenyl)-isoxazole are added in portions to a solution of 2.3 g (0.1 g atom) of sodium in 100 ml of absolute ethanol in the course of about 30 minutes while cooling with ice and stirring. The mixture is then stirred at room temperature for 1 hour, the alcohol is distilled off in vacuo, the residue is dissolved in about 1 liter of warm water, the solution is extracted twice with methylene chloride, the aqueous phase is acidified to pH=4 with 10 per cent strength hydrochloric acid (~38 ml) and the precipitate is filtered off cold with suction and dried in vacuo at 50° C. 21.7 g (93%) of 2,4-dichloro5-fluoro-benzoylacetonitrile of melting point 98°-99° C. are obtained. while cooling with ice The mixture is then stirred at room temperature for 1 hour the alcohol is distilled off in vacuo the residue is dissolved in about 1 liter of warm water the solution is extracted twice with methylene chloride the precipitate is filtered off cold with suction dried in vacuo at 50° C

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 21 g of 2,4-dichloro-5-fluoro-benzoyl-acetonitrile, 19.2 g of methyl o-formate and 23.1 g of acetic anhydride is refluxed at a bath temperature of 150° C. for 3 hours. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C. 24.5 g (99%) of 2-(2,4-dichloro-5-fluoro-benzoyl)-3-methoxy-acrylonitrile are obtained. A sample recrystallized from toluene gives colorless crystals of melting point 159° C. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C

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

実験手順: A mixture of 47.4 g of ethyl 2,4-dichloro-5-fluoro-benzoate and 8.2 g of anhydrous acetonitrile are added dropwise to a suspension of 6.1 g of 80% strength sodium hydride in 100 ml of anhydrous tetrahydrofuran under reflux in the course of about 1 hour. The mixture is heated at the boiling point under reflux for a further hour and cooled to room temperature, and 150 ml of ether are added. The precipitate is filtered off with suction and dissolved in 50 ml of ice-water and the solution is acidified to pH=6 with 10% strength hydrochloric acid. The precipitate is filtered off cold with suction, rinsed with ice-water and dried in vacuo at 40° C. 16 g of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 96°-98° C. are obtained. under reflux in the course of about 1 hour The mixture is heated at the boiling point under reflux for a further hour The precipitate is filtered off with suction dissolved in 50 ml of ice-water The precipitate is filtered off cold with suction rinsed with ice-water dried in vacuo at 40° C

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

実験手順: A mixture of 47.4 g of ethyl 2,4-dichloro-5-fluoro-benzoate and 8.2 g of anhydrous acetonitrile are added dropwise to a suspension of 6.1 g of 80% strength sodium hydride in 100 ml of anhydrous tetrahydrofuran under reflux in the course of about 1 hour. The mixture is heated at the boiling point under reflux for a further hour and cooled to room temperature, and 150 ml of ether are added. The precipitate is filtered off with suction and dissolved in 50 ml of ice-water and the solution is acidified to pH=6 with 10% strength hydrochloric acid. The precipitate is filtered off cold with suction, rinsed with ice-water and dried in vacuo at 40° C. 16 g of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 96°-98° C. are obtained. under reflux in the course of about 1 hour The mixture is heated at the boiling point under reflux for a further hour The precipitate is filtered off with suction dissolved in 50 ml of ice-water The precipitate is filtered off cold with suction rinsed with ice-water dried in vacuo at 40° C

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

実験手順: A mixture of 47.4 g of ethyl 2,4-dichloro-5-fluoro-benzoate and 8.2 g of anhydrous acetonitrile are added dropwise to a suspension of 6.1 g of 80% strength sodium hydride in 100 ml of anhydrous tetrahydrofuran under reflux in the course of about 1 hour. The mixture is heated at the boiling point under reflux for a further hour and cooled to room temperature, and 150 ml of ether are added. The precipitate is filtered off with suction and dissolved in 50 ml of ice-water and the solution is acidified to pH=6 with 10% strength hydrochloric acid. The precipitate is filtered off cold with suction, rinsed with ice-water and dried in vacuo at 40° C. 16 g of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 96°-98° C. are obtained. under reflux in the course of about 1 hour The mixture is heated at the boiling point under reflux for a further hour The precipitate is filtered off with suction dissolved in 50 ml of ice-water The precipitate is filtered off cold with suction rinsed with ice-water dried in vacuo at 40° C

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

実験手順: 23.2 g (0.1 mole) of 5-(2,4-dichloro-5-fluoro-phenyl)-isoxazole are added in portions to a solution of 2.3 g (0.1 g atom) of sodium in 100 ml of absolute ethanol in the course of about 30 minutes while cooling with ice and stirring. The mixture is then stirred at room temperature for 1 hour, the alcohol is distilled off in vacuo, the residue is dissolved in about 1 litre of warm water, the solution is extracted twice with methylene chloride, the aqueous phase is acidified to pH=4 with 10 per cent strength hydrochloric acid (~38 ml) and the precipitate is filtered off cold with suction and dried in vacuo at 50° C. 21.7 g (93%) of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 98°-99° C. are obtained. while cooling with ice The mixture is then stirred at room temperature for 1 hour the alcohol is distilled off in vacuo the residue is dissolved in about 1 litre of warm water the solution is extracted twice with methylene chloride the precipitate is filtered off cold with suction dried in vacuo at 50° C

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

実験手順: 23.2 g (0.1 mole) of 5-(2,4-dichloro-5-fluoro-phenyl)-isoxazole are added in portions to a solution of 2.3 g (0.1 g atom) of sodium in 100 ml of absolute ethanol in the course of about 30 minutes while cooling with ice and stirring. The mixture is then stirred at room temperature for 1 hour, the alcohol is distilled off in vacuo, the residue is dissolved in about 1 litre of warm water, the solution is extracted twice with methylene chloride, the aqueous phase is acidified to pH=4 with 10 per cent strength hydrochloric acid (~38 ml) and the precipitate is filtered off cold with suction and dried in vacuo at 50° C. 21.7 g (93%) of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 98°-99° C. are obtained. while cooling with ice The mixture is then stirred at room temperature for 1 hour the alcohol is distilled off in vacuo the residue is dissolved in about 1 litre of warm water the solution is extracted twice with methylene chloride the precipitate is filtered off cold with suction dried in vacuo at 50° C

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

実験手順: 23.2 g (0.1 mole) of 5-(2,4-dichloro-5-fluoro-phenyl)-isoxazole are added in portions to a solution of 2.3 g (0.1 g atom) of sodium in 100 ml of absolute ethanol in the course of about 30 minutes while cooling with ice and stirring. The mixture is then stirred at room temperature for 1 hour, the alcohol is distilled off in vacuo, the residue is dissolved in about 1 litre of warm water, the solution is extracted twice with methylene chloride, the aqueous phase is acidified to pH=4 with 10 per cent strength hydrochloric acid (~38 ml) and the precipitate is filtered off cold with suction and dried in vacuo at 50° C. 21.7 g (93%) of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 98°-99° C. are obtained. while cooling with ice The mixture is then stirred at room temperature for 1 hour the alcohol is distilled off in vacuo the residue is dissolved in about 1 litre of warm water the solution is extracted twice with methylene chloride the precipitate is filtered off cold with suction dried in vacuo at 50° C

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 21 g of 2,4-dichloro-5-fluorobenzoyl-acetonitrile, 19.2 g of methyl o-formate and 23.1 g of acetic anhydride is refluxed at a bath temperature of 150° C. for 3 hours. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C. 24.5 g (99%) of 2-(2,4-dichloro-5-fluorobenzoyl)-3-methoxy-acrylonitrile are obtained. A sample recrystallized from toluene gives colorless crystals of melting point 159° C. The volatile constituents are then distilled off under a waterpump vacuum and finally under a fine vacuum at a bath temperature of 120° C

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

実験手順: A mixture of 47.4 g of ethyl 2,4-dichloro-5-fluoro-benzoate and 8.2 g of anhydrous acetonitrile are added dropwise to a suspension of 6.1 g of 80% strength sodium hydride in 100 ml of anhydrous tetrahydrofuran under reflux in the course of about 1 hour. The mixture is heated at the boiling point under reflux for a further hour and cooled to room temperature, and 150 ml of ether are added. The precipitate is filtered off with suction and dissolved in 50 ml of ice-water and the solution is acidified to pH=6 with 10% strength hydrochloric acid. The precipitate is filtered off cold with suction, rinsed with ice-water and dried in vacuo at 40° C. 16 g of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 96°-98° C. are obtained. under reflux in the course of about 1 hour The mixture is heated at the boiling point under reflux for a further hour The precipitate is filtered off with suction dissolved in 50 ml of ice-water The precipitate is filtered off cold with suction rinsed with ice-water dried in vacuo at 40° C

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

実験手順: 23.2 g (0.1 mole) of 5-(2,4-dichloro-5-fluorophenyl)-isoxazole are added in portions to a solution of 2.3 g (0.1 g atom) of sodium in 100 ml of absolute ethanol in the course of about 30 minutes while cooling with ice and stirring. The mixture is then stirred at room temperature for 1 hour, the alcohol is distilled off in vacuo, the residue is dissolved in about 1 litre of warm water, the solution is extracted twice with methylene chloride, the aqueous phase is acidified to pH=4 with 10 per cent strength hydrochloric acid (~38 ml) and the precipitate is filtered off cold with suction and dried in vacuo at 50° C. 21.7 g (93%) of 2,4-dichloro-5-fluoro-benzoylacetonitrile of melting point 98°-99° C. are obtained. while cooling with ice The mixture is then stirred at room temperature for 1 hour the alcohol is distilled off in vacuo the residue is dissolved in about 1 litre of warm water the solution is extracted twice with methylene chloride the precipitate is filtered off cold with suction dried in vacuo at 50° C