2-bromo-4-chlorobenzonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: 13.9 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 2-bromo-4-chlorobenzonitrile (Example 65A) in 60 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and under ice cooling 20 ml of 1N hydrochloric acid are added dropwise. The mixture is heated under reflux for 1 h and left to cool. For the work-up the solution is adjusted to an alkaline pH with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The crude product is reacted further without purification. 13.9 ml of borane-THF complex are provided under ice cooling The reaction mixture is then heated for 1 h under reflux are added dropwise The mixture is heated under reflux for 1 h left to cool extracted with dichloromethane The organic phase is dried over sodium sulfate concentrated on a rotary evaporator The crude product is reacted further without purification

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

実験手順: 13.9 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 2-bromo-4-chlorobenzonitrile (Example 65A) in 60 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and under ice cooling 20 ml of 1N hydrochloric acid are added dropwise. The mixture is heated under reflux for 1 h and left to cool. For the work-up the solution is adjusted to an alkaline pH with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The crude product is reacted further without purification. 13.9 ml of borane-THF complex are provided under ice cooling The reaction mixture is then heated for 1 h under reflux are added dropwise The mixture is heated under reflux for 1 h left to cool extracted with dichloromethane The organic phase is dried over sodium sulfate concentrated on a rotary evaporator The crude product is reacted further without purification

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

実験手順: 588 mg of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanole and deposited onto 364 mg of aluminum oxide on a rotary evaporator. The residue is irradiated for 60 min in a microwave at 150° C. After cooling the residue is stirred with ethyl acetate and water, the mixture is filtered and the aqueous phase is removed. The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product is reacted further without additional purification. deposited onto 364 mg of aluminum oxide on a rotary evaporator The residue is irradiated for 60 min in a microwave at 150° C After cooling the residue the mixture is filtered the aqueous phase is removed The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum The product is reacted further without additional purification

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

実験手順: 588 mg of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanole and deposited onto 364 mg of aluminum oxide on a rotary evaporator. The residue is irradiated for 60 min in a microwave at 150° C. After cooling the residue is stirred with ethyl acetate and water, the mixture is filtered and the aqueous phase is removed. The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product is reacted further without additional purification. deposited onto 364 mg of aluminum oxide on a rotary evaporator The residue is irradiated for 60 min in a microwave at 150° C After cooling the residue the mixture is filtered the aqueous phase is removed The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum The product is reacted further without additional purification

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

実験手順: 13.9 ml (13.9 mmol) of borane-THF complex (1 M) are provided with ice cooling. Slowly a solution of 604 mg (2.8 mmol) of 2-bromo-4-chlorobenzonitrile (Example 1A) in 60 ml of THF is added. Thereafter the reaction mixture is heated under reflux for 1 h, cooled, and 20 ml of 1N hydrochloric acid are added dropwise with ice cooling. For the work up, the solution is rendered alkaline with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The crude product (450 mg, about 73% pure) is reacted further without purification. 13.9 ml (13.9 mmol) of borane-THF complex (1 M) are provided with ice cooling Thereafter the reaction mixture is heated under reflux for 1 h cooled extracted with dichloromethane The organic phase is dried over sodium sulfate concentrated on a rotary evaporator The crude product (450 mg, about 73% pure) is reacted further without purification

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

実験手順: 588 mg (2.5 mmol) of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanol and concentrated onto 364 mg of alumina (neutral) on a rotary evaporator. The residue is microwaved at 150° C. for a total of 60 min. After cooling, the residue is stirred with ethyl acetate and water, filtered, and the aqueous phase is separated. The organic phase is washed with a sodium hydrogen carbonate solution, dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification. concentrated onto 364 mg of alumina (neutral) on a rotary evaporator The residue is microwaved at 150° C. for a total of 60 min After cooling filtered the aqueous phase is separated The organic phase is washed with a sodium hydrogen carbonate solution dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum The product (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification

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

実験手順: 588 mg (2.5 mmol) of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanol and concentrated onto 364 mg of alumina (neutral) on a rotary evaporator. The residue is microwaved at 150° C. for a total of 60 min. After cooling, the residue is stirred with ethyl acetate and water, filtered, and the aqueous phase is separated. The organic phase is washed with a sodium hydrogen carbonate solution, dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification. concentrated onto 364 mg of alumina (neutral) on a rotary evaporator The residue is microwaved at 150° C. for a total of 60 min After cooling filtered the aqueous phase is separated The organic phase is washed with a sodium hydrogen carbonate solution dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum The product (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification

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

実験手順: 13.9 ml of borane-THF complex are provided under ice cooling. A solution of 2.0 g of 2-bromo-4-chlorobenzonitrile (Example 65A) in 60 ml of THF is added slowly. The reaction mixture is then heated for 1 h under reflux, cooled and under ice cooling 20 ml of 1N hydrochloric acid are added dropwise. The mixture is heated under reflux for 1 h and left to cool. For the work-up the solution is adjusted to an alkaline pH with a 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The crude product is reacted further without purification. 13.9 ml of borane-THF complex are provided under ice cooling The reaction mixture is then heated for 1 h under reflux are added dropwise The mixture is heated under reflux for 1 h left to cool extracted with dichloromethane The organic phase is dried over sodium sulfate concentrated on a rotary evaporator The crude product is reacted further without purification

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

実験手順: 588 mg of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanole and deposited onto 364 mg of aluminum oxide on a rotary evaporator. The residue is irradiated for 60 min in a microwave at 150° C. After cooling the residue is stirred with ethyl acetate and water, the mixture is filtered and the aqueous phase is removed. The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product is reacted further without additional purification. deposited onto 364 mg of aluminum oxide on a rotary evaporator The residue is irradiated for 60 min in a microwave at 150° C After cooling the residue the mixture is filtered the aqueous phase is removed The organic phase is washed with a sodium hydrogencarbonate solution dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum The product is reacted further without additional purification