2-[4-(bromomethyl)phenyl]acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.446 mL (5.44 mmol) of pyrrolidine and 1.366 g (9.882 mmol) of potassium carbonate are added to 20 mL of dimethylformamide. 1.038 g (4.941 mmol) of (4-bromomethyl-phenyl)-acetonitrile are added with stirring and the mixture is stirred for 12 hours at RT. The reaction mixture is evaporated down in the rotary evaporator and the residue is extracted with EtOAc and water. The organic phase is dried over magnesium sulphate and the solvent is removed using the rotary evaporator. the mixture is stirred for 12 hours at RT The reaction mixture is evaporated down in the rotary evaporator the residue is extracted with EtOAc and water The organic phase is dried over magnesium sulphate the solvent is removed the rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.446 mL (5.44 mmol) of pyrrolidine and 1.366 g (9.882 mmol) of potassium carbonate are added to 20 mL of dimethylformamide. 1.038 g (4.941 mmol) of (4-bromomethyl-phenyl)-acetonitrile are added with stirring and the mixture is stirred for 12 hours at RT. The reaction mixture is evaporated down in the rotary evaporator and the residue is extracted with EtOAc and water. The organic phase is dried over magnesium sulphate and the solvent is removed using the rotary evaporator. the mixture is stirred for 12 hours at RT The reaction mixture is evaporated down in the rotary evaporator the residue is extracted with EtOAc and water The organic phase is dried over magnesium sulphate the solvent is removed the rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.86 mL (9 mmol) of phosphorus tribromide are added dropwise to a solution of 2.6 g (17.66 mmol) of (4-hydroxymethyl-phenyl)-acetonitrile in 25 mL MTBE at 0° C. After the reaction has ended the reaction mixture is combined with water at RT, the organic phase is separated off and these are extracted successively with sodium hydrogen carbonate solution and water. The organic phase is dried over magnesium sulphate and the solvent is distilled off using the rotary evaporator. the organic phase is separated off these are extracted successively with sodium hydrogen carbonate solution and water The organic phase is dried over magnesium sulphate the solvent is distilled off the rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1 liter round bottomed flask with condenser and thermometer 8.2 g of 4-bromomethylbenzylcyanide are dissolved in 453 ml methanol and cooled to +3° C. At this temperature 12.7 ml of 40% dimethylamine solution are added drop-by-drop. The solution is subsequently stirred for 1/4 hour at +5° C. and 2 hours at room temperature. The reaction sequence is controlled by means of thin-layer chromatography (0.57 ml of specimen+0.43 ml methanol: eluent n-butanol: acetic acid: water=4:1:1; v/v; 10 μl coating; HPTLC finished plated diatomaceous earth 60 F 254). Following removal of the volatile components is a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid and extracted with a total of 150 ml of diethyl ether. The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) and extracted subsequently with 250 ml of diethyl ether. The organic phase is washed to neutrality with a saturated solution of common salt, dried with sodium sulfate and evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr). cooled to +3° C removal of the volatile components a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid extracted with a total of 150 ml of diethyl ether The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) extracted subsequently with 250 ml of diethyl ether The organic phase is washed to neutrality with a saturated solution of common salt dried with sodium sulfate evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1 liter round bottomed flask with condenser and thermometer 8.2 g of 4-bromomethylbenzylcyanide are dissolved in 453 ml methanol and cooled to +3° C. At this temperature 12.7 ml of 40% dimethylamine solution are added drop-by-drop. The solution is subsequently stirred for 1/4 hour at +5° C. and 2 hours at room temperature. The reaction sequence is controlled by means of thin-layer chromatography (0.57 ml of specimen+0.43 ml methanol: eluent n-butanol: acetic acid: water=4:1:1; v/v; 10 μl coating; HPTLC finished plated diatomaceous earth 60 F 254). Following removal of the volatile components is a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid and extracted with a total of 150 ml of diethyl ether. The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) and extracted subsequently with 250 ml of diethyl ether. The organic phase is washed to neutrality with a saturated solution of common salt, dried with sodium sulfate and evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr). cooled to +3° C removal of the volatile components a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid extracted with a total of 150 ml of diethyl ether The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) extracted subsequently with 250 ml of diethyl ether The organic phase is washed to neutrality with a saturated solution of common salt dried with sodium sulfate evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.79 g (50.93 mmol) of 3-nitrophthalimide are dissolved in 450 ml of DMF, and 10.56 g (76.39 mmol) of potassium carbonate are added. The suspension is treated with ultrasound for 10 min. 10.7 g (50.93 mmol) of 2-[4-(bromomethyl)phenyl]acetonitrile (obtained by reaction of 2-(4-methylphenyl)acetonitrile with N-bromosuccinimide (NBS) and azobisisobutyronitrile (AIBN) in carbon tetrachloride, cf. E. Laurent, B. Marquet, R. Tardivel; Tetrahedron; 47; 24; 1991; pp. 3969-3980) are then added, and the reaction mixture is stirred at room temperature for 20 h. The suspension is then poured into a mixture of 300 ml of 2 N hydrochloric acid and 3 l of water. The crystals formed are filtered off with suction, washed with water and dried under reduced pressure. This gives 12 g (73% of theory) of the desired compound. Rf (SiO2, CH2Cl2/EtOH=100/1)=0.55, MS=322.2 (M+H+). The suspension is treated with ultrasound for 10 min

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.79 g (50.93 mmol) of 3-nitrophthalimide are dissolved in 450 ml of DMF, and 10.56 g (76.39 mmol) of potassium carbonate are added. The suspension is treated with ultrasound for 10 min. 10.7 g (50.93 mmol) of 2-[4-(bromomethyl)phenyl]acetonitrile (obtained by reaction of 2-(4-methylphenyl)acetonitrile with N-bromosuccinimide (NBS) and azobisisobutyronitrile (AIBN) in carbon tetrachloride, cf. E. Laurent, B. Marquet, R. Tardivel; Tetrahedron; 47; 24; 1991; pp. 3969-3980) are then added, and the reaction mixture is stirred at room temperature for 20 h. The suspension is then poured into a mixture of 300 ml of 2 N hydrochloric acid and 3 l of water. The crystals formed are filtered off with suction, washed with water and dried under reduced pressure. This gives 12 g (73% of theory) of the desired compound. Rf (SiO2, CH2Cl2/EtOH=100/1)=0.55, MS=322.2 (M+H+). The suspension is treated with ultrasound for 10 min

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.446 mL (5.44 mmol) of pyrrolidine and 1.366 g (9.882 mmol) of potassium carbonate are added to 20 mL of dimethylformamide. 1.038 g (4.941 mmol) of (4-bromomethyl-phenyl)-acetonitrile are added with stirring and the mixture is stirred for 12 hours at RT. The reaction mixture is evaporated down in the rotary evaporator and the residue is extracted with EtOAc and water. The organic phase is dried over magnesium sulphate and the solvent is removed using the rotary evaporator. the mixture is stirred for 12 hours at RT The reaction mixture is evaporated down in the rotary evaporator the residue is extracted with EtOAc and water The organic phase is dried over magnesium sulphate the solvent is removed the rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.86 mL (9 mmol) of phosphorus tribromide are added dropwise to a solution of 2.6 g (17.66 mmol) of (4-hydroxymethyl-phenyl)-acetonitrile in 25 mL MTBE at 0° C. After the reaction has ended the reaction mixture is combined with water at RT, the organic phase is separated off and these are extracted successively with sodium hydrogen carbonate solution and water. The organic phase is dried over magnesium sulphate and the solvent is distilled off using the rotary evaporator. the organic phase is separated off these are extracted successively with sodium hydrogen carbonate solution and water The organic phase is dried over magnesium sulphate the solvent is distilled off the rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1 liter round bottomed flask with condenser and thermometer 8.2 g of 4-bromomethylbenzylcyanide are dissolved in 453 ml methanol and cooled to +3° C. At this temperature 12.7 ml of 40% dimethylamine solution are added drop-by-drop. The solution is subsequently stirred for 1/4 hour at +5° C. and 2 hours at room temperature. The reaction sequence is controlled by means of thin-layer chromatography (0.57 ml of specimen+0.43 ml methanol: eluent n-butanol: acetic acid: water=4:1:1; v/v; 10 μl coating; HPTLC finished plated diatomaceous earth 60 F 254). Following removal of the volatile components is a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid and extracted with a total of 150 ml of diethyl ether. The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) and extracted subsequently with 250 ml of diethyl ether. The organic phase is washed to neutrality with a saturated solution of common salt, dried with sodium sulfate and evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr). cooled to +3° C removal of the volatile components a rotary evaporator (20 torr, 40° C. bath temperature) the residue is absorbed in 20 ml 1N hydrochloric acid extracted with a total of 150 ml of diethyl ether The clear, aqueous phase is treated with 30 ml of 1N sodium hydroxide solution (ice cold) extracted subsequently with 250 ml of diethyl ether The organic phase is washed to neutrality with a saturated solution of common salt dried with sodium sulfate evaporated to dryness in a rotary evaporator (30° C. bath temperature, 20 torr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.79 g (50.93 mmol) of 3-nitrophthalimide are dissolved in 450 ml of DMF, and 10.56 g (76.39 mmol) of potassium carbonate are added. The suspension is treated with ultrasound for 10 min. 10.7 g (50.93 mmol) of 2-[4-(bromomethyl)phenyl]acetonitrile (obtained by reaction of 2-(4-methylphenyl)acetonitrile with N-bromosuccinimide (NBS) and azobisisobutyronitrile (AIBN) in carbon tetrachloride, cf. E. Laurent, B. Marquet, R. Tardivel; Tetrahedron; 47; 24; 1991; pp. 3969-3980) are then added, and the reaction mixture is stirred at room temperature for 20 h. The suspension is then poured into a mixture of 300 ml of 2 N hydrochloric acid and 3 l of water. The crystals formed are filtered off with suction, washed with water and dried under reduced pressure. This gives 12 g (73% of theory) of the desired compound. Rf (SiO2, CH2Cl2/EtOH=100/1)=0.55, MS=322.2 (M+H+). The suspension is treated with ultrasound for 10 min