3-(2-bromophenyl)propanenitrile

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

Procedure: Into a 250-mL 3-necked round-bottom flask, was placed a solution of 3-(2-bromophenyl)propanenitrile (2.1 g, 10.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of borane (1 mol/L in THF, 50 mL, 5.00 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water at 0° C. and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride. The aqueous solution was extracted with 30 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous solution was adjusted to 10 with 10% aqueous sodium hydroxide. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil. Into a 250-mL 3-necked round-bottom flask, was placed with stiffing at 0° C The reaction was then quenched by the addition of 50 mL of water at 0° C. extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride The aqueous solution was extracted with 30 mL of ethyl acetate The resulting solution was extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil

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

Procedure: Into a 250-mL 3-necked round-bottom flask, was placed a solution of 3-(2-bromophenyl)propanenitrile (2.1 g, 10.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of borane (1 mol/L in THF, 50 mL, 5.00 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water at 0° C. and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride. The aqueous solution was extracted with 30 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous solution was adjusted to 10 with 10% aqueous sodium hydroxide. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil. Into a 250-mL 3-necked round-bottom flask, was placed with stiffing at 0° C The reaction was then quenched by the addition of 50 mL of water at 0° C. extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride The aqueous solution was extracted with 30 mL of ethyl acetate The resulting solution was extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500-mL 3-necked round-bottom flask, was placed a solution of acetonitrile (49 g, 1.20 mol, 9.96 equiv) in tetrahydrofuran (150 mL). This was followed by the addition of BuLi (72 mL, 1.50 equiv) dropwise with stirring at −78° C. Stirred at −78° C. for 1 h. To this was added a solution of 1-bromo-2-(bromomethyl)benzene (30 g, 120.00 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) dropwise with stiffing at −78° C. The resulting solution was stirred for 1 h at −78° C. The reaction was quenched by the addition of 100 mL of water at −78° C. The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). The crude product was purified by distillation under reduced pressure (2 mm Hg) and the fraction was collected at 98-107° C. This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil. Into a 500-mL 3-necked round-bottom flask, was placed Stirred at −78° C. for 1 h with stiffing at −78° C The resulting solution was stirred for 1 h at −78° C The reaction was quenched by the addition of 100 mL of water at −78° C The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The crude product was purified by distillation under reduced pressure (2 mm Hg) the fraction was collected at 98-107° C This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil

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

Procedure: To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in Benzene (0.064M) at room temperature was added acetone cyanohydrin (1.5 eq), 1-1′(Azodicarbonyl)dipiperidine (1.5 eq) then dropwise over 5 min triphenyl phosphine (1.5 eq). The mixture was stirred at room temperature for 12 h, diluted with hexane (0.03M) and filtered on pad of silica gel. Fractions containing the desired material were combined and concentrated. A second purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 30%, in 30 min) afforded the desired compound as a colorless oil. filtered on pad of silica gel Fractions containing the desired material concentrated A second purification by column chromatography on silica gel (Combi-Flash by ISCO) eluting with Hex/EtOAc (0 to 30%, in 30 min)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 250-mL 3-necked round-bottom flask, was placed a solution of 3-(2-bromophenyl)propanenitrile (2.1 g, 10.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of borane (1 mol/L in THF, 50 mL, 5.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water at 0° C. and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride. The aqueous solution was extracted with 30 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous solution was adjusted to 10 with 10% aqueous sodium hydroxide. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil. Into a 250-mL 3-necked round-bottom flask, was placed The resulting solution was stirred for overnight at room temperature The reaction was then quenched by the addition of 50 mL of water at 0° C. extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride The aqueous solution was extracted with 30 mL of ethyl acetate The resulting solution was extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500-mL 3-necked round-bottom flask, was placed a solution of acetonitrile (49 g, 1.20 mol, 9.96 equiv) in tetrahydrofuran (150 mL). This was followed by the addition of BuLi (72 mL, 1.50 equiv) dropwise with stirring at −78° C. Stirred at −78° C. for 1 h. To this was added a solution of 1-bromo-2-(bromomethyl)benzene (30 g, 120.00 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) dropwise with stirring at −78° C. The resulting solution was stirred for 1 h at −78° C. The reaction was quenched by the addition of 100 mL of water at −78° C. The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). The crude product was purified by distillation under reduced pressure (2 mm Hg) and the fraction was collected at 98-107° C. This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil. Into a 500-mL 3-necked round-bottom flask, was placed Stirred at −78° C. for 1 h with stirring at −78° C The resulting solution was stirred for 1 h at −78° C The reaction was quenched by the addition of 100 mL of water at −78° C The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The crude product was purified by distillation under reduced pressure (2 mm Hg) the fraction was collected at 98-107° C This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil

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

Procedure: Into a 250-mL 3-necked round-bottom flask, was placed a solution of 3-(2-bromophenyl)propanenitrile (2.1 g, 10.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of borane (1 mol/L in THF, 50 mL, 5.00 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water at 0° C. and extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride. The aqueous solution was extracted with 30 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous solution was adjusted to 10 with 10% aqueous sodium hydroxide. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, concentrated under vacuum. This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil. Into a 250-mL 3-necked round-bottom flask, was placed with stiffing at 0° C The reaction was then quenched by the addition of 50 mL of water at 0° C. extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The residue was dissolved in 30 mL of 6N aqueous hydrogen chloride The aqueous solution was extracted with 30 mL of ethyl acetate The resulting solution was extracted with 3×50 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum This resulted in 1.3 g (58%) of 3-(2-bromophenyl)propan-1-amine as colorless oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500-mL 3-necked round-bottom flask, was placed a solution of acetonitrile (49 g, 1.20 mol, 9.96 equiv) in tetrahydrofuran (150 mL). This was followed by the addition of BuLi (72 mL, 1.50 equiv) dropwise with stirring at −78° C. Stirred at −78° C. for 1 h. To this was added a solution of 1-bromo-2-(bromomethyl)benzene (30 g, 120.00 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) dropwise with stiffing at −78° C. The resulting solution was stirred for 1 h at −78° C. The reaction was quenched by the addition of 100 mL of water at −78° C. The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). The crude product was purified by distillation under reduced pressure (2 mm Hg) and the fraction was collected at 98-107° C. This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil. Into a 500-mL 3-necked round-bottom flask, was placed Stirred at −78° C. for 1 h with stiffing at −78° C The resulting solution was stirred for 1 h at −78° C The reaction was quenched by the addition of 100 mL of water at −78° C The resulting aqueous solution was extracted with 3×100 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum The crude product was purified by distillation under reduced pressure (2 mm Hg) the fraction was collected at 98-107° C This resulted in 13.21 g (52%) of 3-(2-bromophenyl)propanenitrile as colorless oil