No renderable structure data available
C1=CC(=C(C=C1C(=O)N)Br)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-bromo-4-chlorobenzamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 791137-22-9 |
| Database ID | 53216663 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-bromo-4-chlorobenzamide (CAS 791137-22-9) 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 53216663
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-4116aeb6adf64e46a491a15d08b37bc8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-acbf84dc7fac47528e1b7f086a15357cConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until the pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc. The aqueous phase was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time). the reaction cautiously quenched with ethanol When bubbling 1N HCl was added until the pH was ˜2 The mixture was partitioned between EtOAc and water The aqueous phase was washed 3× with EtOAc extracted 3× with EtOAc The combined organics phases were washed with brine dried over anhydrous Na2SO4 filtered evaporated
Source ID: ord-d7b6c678e7b94a8a8022c55a8915f230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chlorobenzoic acid (2.35 g, 10 mmol) was suspended in CH2Cl2 (50 mL) and stirred under argon at room temperature. Oxalyl chloride (2.53 g, 20 mmol) was added followed by DMF (10 μL). Gas evolution began, and the mixture was stirred until gas evolution ceased. The solvents were pumped off and toluene was added and stripped off to remove excess oxalyl chloride. The residue was taken up in EtOAc and added to concentrated ammonium hydroxide (10 mL). This was stirred for 30 min. The phases were separated and the organic washed 1× with brine dried over anhydrous Na2SO4, filtered, and evaporated. The residue was crystallized from EtOAc/hexane to give the title compound as a white crystalline solid. LC-MS m/z 233.7 (M+H)+, 1.54 min (ret time); mp 146-147° C.; analytical HPLC shows 100% purity, (ret time: 11.835 min). the mixture was stirred until gas evolution to remove excess oxalyl chloride added to concentrated ammonium hydroxide (10 mL) This was stirred for 30 min The phases were separated the organic washed 1× with brine dried over anhydrous Na2SO4 filtered evaporated The residue was crystallized from EtOAc/hexane
Source ID: ord-d54d3782a97541f38a04fe3423f31953Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until the pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc. The aqueous phase was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time). the reaction cautiously quenched with ethanol When bubbling 1N HCl was added until the pH was ˜2 The mixture was partitioned between EtOAc and water The aqueous phase was washed 3× with EtOAc extracted 3× with EtOAc The combined organics phases were washed with brine dried over anhydrous Na2SO4 filtered evaporated
Source ID: ord-2111612c195645ad9d92bbf8fd1a5fc4Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until the pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc. The aqueous phase was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time). the reaction cautiously quenched with ethanol When bubbling 1N HCl was added until the pH was ˜2 The mixture was partitioned between EtOAc and water The aqueous phase was washed 3× with EtOAc extracted 3× with EtOAc The combined organics phases were washed with brine dried over anhydrous Na2SO4 filtered evaporated
Source ID: ord-2111612c195645ad9d92bbf8fd1a5fc4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chlorobenzoic acid (2.35 g, 10 mmol) was suspended in CH2Cl2 (50 mL) and stirred under argon at room temperature. Oxalyl chloride (2.53 g, 20 mmol) was added followed by DMF (10 μL). Gas evolution began, and the mixture was stirred until gas evolution ceased. The solvents were pumped off and toluene was added and stripped off to remove excess oxalyl chloride. The residue was taken up in EtOAc and added to concentrated ammonium hydroxide (10 mL). This was stirred for 30 min. The phases were separated and the organic washed 1× with brine dried over anhydrous Na2SO4, filtered, and evaporated. The residue was crystallized from EtOAc/hexane to give the title compound as a white crystalline solid. LC-MS m/z 233.7 (M+H)+, 1.54 min (ret time); mp 146-147° C.; analytical HPLC shows 100% purity, (ret time: 11.835 min). the mixture was stirred until gas evolution to remove excess oxalyl chloride added to concentrated ammonium hydroxide (10 mL) This was stirred for 30 min The phases were separated the organic washed 1× with brine dried over anhydrous Na2SO4 filtered evaporated The residue was crystallized from EtOAc/hexane
Source ID: ord-4b24794518394da3a50e4a633c876fc7Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtoAC. The aqueous was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine (1×) and dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time). the reaction cautiously quenched with ethanol When bubbling 1N HCl was added until pH was ˜2 The mixture was partitioned between EtOAc and water The aqueous phase was washed 3× with EtoAC extracted 3× with EtOAc The combined organics phases were washed with brine (1×) dried over anhydrous Na2SO4 filtered concentrated
Source ID: ord-ed78bd4603144d18a6f6e3ceea211d2dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtoAC. The aqueous was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine (1×) and dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time). the reaction cautiously quenched with ethanol When bubbling 1N HCl was added until pH was ˜2 The mixture was partitioned between EtOAc and water The aqueous phase was washed 3× with EtoAC extracted 3× with EtOAc The combined organics phases were washed with brine (1×) dried over anhydrous Na2SO4 filtered concentrated
Source ID: ord-ed78bd4603144d18a6f6e3ceea211d2dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chlorobenzoic acid (2.35 g, 10 mmol) was suspended in CH2Cl2 (50 mL) and stirred under argon at room temperature. Oxalyl chloride (2.53 g, 20 mmol) was added followed by DMF (10 μL). Gas evolution began, and the mixture was stirred until gas evolution ceased. The solvents were pumped off and toluene was added and stripped off to remove excess oxalyl chloride. The residue was taken up in EtOAc and added to concentrated ammonium hydroxide (10 mL). This was stirred for thirty min. The phases were separated and the organic washed 1× with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was crystallized from EtOAc/hexane to give the title compound as a white crystalline solid. LC-MS m/z 233.7 (M+H)+, 1.54 min (ret time); mp 146-147° C.; analytical HPLC shows 100% purity, (ret time 11.835 min). the mixture was stirred until gas evolution to remove excess oxalyl chloride added to concentrated ammonium hydroxide (10 mL) This was stirred for thirty min The phases were separated the organic washed 1× with brine dried over anhydrous Na2SO4 filtered concentrated The residue was crystallized from EtOAc/hexane
Source ID: ord-01c311ea49864740973c30fb5ff9c510Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4116aeb6adf64e46a491a15d08b37bc8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-acbf84dc7fac47528e1b7f086a15357cPubChem References
These sources are listed in the compound's public database record.
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