No renderable structure data available
C1=CC(=CC(=C1)Br)CCC(=O)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(3-bromophenyl)propanamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 615534-55-9 |
| Database ID | 20823841 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(3-bromophenyl)propanamide (CAS 615534-55-9) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 20823841
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d29ea5db254849ee9b427f04b41520c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-08a834a0b0fe46a48ef40c9076665ca6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The precipitate was removed by filtration the filtrate was cooled in an ice bath Ammonia gas was bubbled into the solution for 2 min to warm to room temperature overnight The reaction mixture was concentrated under reduced pressure the residue was dissolved in EtOAc This solution was washed with saturated aqueous NaHCO3 and brine dried over Na2SO4 concentrated under reduced pressure to an oil which was triturated with hexanes The product was collected by filtration
Source ID: ord-3d9ccc428e2b4968b253a57903decff1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The precipitate was removed by filtration the filtrate was cooled in an ice bath Ammonia gas was bubbled into the solution for 2 min to warm to room temperature overnight The reaction mixture was concentrated under reduced pressure the residue was dissolved in EtOAc This solution was washed with saturated aqueous NaHCO3 and brine dried over Na2SO4 concentrated under reduced pressure to an oil which was triturated with hexanes The product was collected by filtration
Source ID: ord-3d9ccc428e2b4968b253a57903decff1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-f4dfc78902b247c68b45d0fa60a28ec0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-f4dfc78902b247c68b45d0fa60a28ec0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The precipitate was removed by filtration the filtrate was cooled in an ice bath Ammonia gas was bubbled into the solution for 2 min to warm to room temperature overnight The reaction mixture was concentrated under reduced pressure the residue was dissolved in EtOAc This solution was washed with saturated aqueous NaHCO3 and brine dried over Na2SO4 concentrated under reduced pressure to an oil which was triturated with hexanes The product was collected by filtration
Source ID: ord-daf5cae856d6436d8ae93669d314b162Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-08a834a0b0fe46a48ef40c9076665ca6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The precipitate was removed by filtration the filtrate was cooled in an ice bath Ammonia gas was bubbled into the solution for 2 min to warm to room temperature overnight The reaction mixture was concentrated under reduced pressure the residue was dissolved in EtOAc This solution was washed with saturated aqueous NaHCO3 and brine dried over Na2SO4 concentrated under reduced pressure to an oil which was triturated with hexanes The product was collected by filtration
Source ID: ord-3d9ccc428e2b4968b253a57903decff1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d29ea5db254849ee9b427f04b41520c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-4df10ea1c0474a85af91badd245917c5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionic acid (93) (5.0 g, 21.8 mmol) and N-hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2Cl2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid. This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The precipitate was removed by filtration the filtrate was cooled in an ice bath Ammonia gas was bubbled into the solution for 2 min to warm to room temperature overnight The reaction mixture was concentrated under reduced pressure the residue was dissolved in EtOAc This solution was washed with saturated aqueous NaHCO3 and brine dried over Na2SO4 concentrated under reduced pressure to an oil which was triturated with hexanes The product was collected by filtration
Source ID: ord-8dba63f1bb8f4a7781f2334f5f6bee52PubChem References
These sources are listed in the compound's public database record.
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