No renderable structure data available
CNC1=C(C(=CC=C1)Br)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-bromo-2-fluoro-N-methylaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 943830-86-2 |
| Database ID | 66606141 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-bromo-2-fluoro-N-methylaniline (CAS 943830-86-2) 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 66606141
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a3b0be501c2e469aba82e3885a18f12bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 3 A solution of 3-bromo-2-fluoro-N-methylaniline (32 mg, 0.157 mmol) and diisopropylamine (0.055 mL, 0.314 mmol) in DCM (2 mL) was treated with 4-fluorobenzoyl chloride (0.028 mL, 0.235 mmol) and the mixture was stirred at rt for 2 h. The mixture was partitioned between DCM and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 80:20 hexane-EtOAc) to provide N-(3-bromo-2-fluorophenyl)-4-fluoro-N-methylbenzamide as a white solid (35 mg, 68%). Mass spectrum m/z 326, 328 (M+H)+. The mixture was partitioned between DCM and NaHCO3 (aq) The organic phase was washed with brine dried concentrated The residue was purified by column chromatography ( eluting with a gradient from 90:10 to 80:20 hexane-EtOAc)
Source ID: ord-c6d12c2a86284487a11d2a13a2b4e40dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 2 A suspension of N-(3-bromo-2-fluorophenyl)formamide (216 mg, 0.991 mmol) in THF (8 mL) was treated with borane dimethyl sulfide complex (2.0 M in THF, 1.486 mL, 2.97 mmol) and the resulting mixture was heated at reflux for 2 h. 1 M hydrochloric acid was added and the mixture was again heated at reflux for 1 h. The mixture was cooled to rt and concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoro-N-methylaniline as a light yellow oil (60 mg, 30%). Mass spectrum m/z 204, 206 (M+H)+. the resulting mixture was heated at reflux for 2 h the mixture was again heated at reflux for 1 h concentrated the residue was partitioned between NaHCO3 (aq) and EtOAc The organic phase was washed with brine dried concentrated
Source ID: ord-918542c33672431d8d3b2814f218d362Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 2 A suspension of N-(3-bromo-2-fluorophenyl)formamide (216 mg, 0.991 mmol) in THF (8 mL) was treated with borane dimethyl sulfide complex (2.0 M in THF, 1.486 mL, 2.97 mmol) and the resulting mixture was heated at reflux for 2 h. 1 M hydrochloric acid was added and the mixture was again heated at reflux for 1 h. The mixture was cooled to rt and concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoro-N-methylaniline as a light yellow oil (60 mg, 30%). Mass spectrum m/z 204, 206 (M+H)+. the resulting mixture was heated at reflux for 2 h the mixture was again heated at reflux for 1 h concentrated the residue was partitioned between NaHCO3 (aq) and EtOAc The organic phase was washed with brine dried concentrated
Source ID: ord-918542c33672431d8d3b2814f218d362Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a3b0be501c2e469aba82e3885a18f12bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 3 A solution of 3-bromo-2-fluoro-N-methylaniline (32 mg, 0.157 mmol) and diisopropylamine (0.055 mL, 0.314 mmol) in DCM (2 mL) was treated with 4-fluorobenzoyl chloride (0.028 mL, 0.235 mmol) and the mixture was stirred at rt for 2 h. The mixture was partitioned between DCM and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 80:20 hexane-EtOAc) to provide N-(3-bromo-2-fluorophenyl)-4-fluoro-N-methylbenzamide as a white solid (35 mg, 68%). Mass spectrum m/z 326, 328 (M+H)+. The mixture was partitioned between DCM and NaHCO3 (aq) The organic phase was washed with brine dried concentrated The residue was purified by column chromatography ( eluting with a gradient from 90:10 to 80:20 hexane-EtOAc)
Source ID: ord-86459f871ab3403db80d7ff7e1d06d73Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 2 A suspension of N-(3-bromo-2-fluorophenyl)formamide (216 mg, 0.991 mmol) in THF (8 mL) was treated with borane dimethyl sulfide complex (2.0 M in THF, 1.486 mL, 2.97 mmol) and the resulting mixture was heated at reflux for 2 h. 1 M hydrochloric acid was added and the mixture was again heated at reflux for 1 h. The mixture was cooled to rt and concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoro-N-methylaniline as a light yellow oil (60 mg, 30%). Mass spectrum m/z 204, 206 (M+H)+. the resulting mixture was heated at reflux for 2 h the mixture was again heated at reflux for 1 h concentrated the residue was partitioned between NaHCO3 (aq) and EtOAc The organic phase was washed with brine dried concentrated
Source ID: ord-341cf64a8f0546eebecd29bea3a36a4bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 3 A solution of 3-bromo-2-fluoro-N-methylaniline (32 mg, 0.157 mmol) and diisopropylamine (0.055 mL, 0.314 mmol) in DCM (2 mL) was treated with 4-fluorobenzoyl chloride (0.028 mL, 0.235 mmol) and the mixture was stirred at rt for 2 h. The mixture was partitioned between DCM and NaHCO3 (aq). The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 80:20 hexane-EtOAc) to provide N-(3-bromo-2-fluorophenyl)-4-fluoro-N-methylbenzamide as a white solid (35 mg, 68%). Mass spectrum m/z 326, 328 (M+H)+. The mixture was partitioned between DCM and NaHCO3 (aq) The organic phase was washed with brine dried concentrated The residue was purified by column chromatography ( eluting with a gradient from 90:10 to 80:20 hexane-EtOAc)
Source ID: ord-c6d12c2a86284487a11d2a13a2b4e40dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Step 2 A suspension of N-(3-bromo-2-fluorophenyl)formamide (216 mg, 0.991 mmol) in THF (8 mL) was treated with borane dimethyl sulfide complex (2.0 M in THF, 1.486 mL, 2.97 mmol) and the resulting mixture was heated at reflux for 2 h. 1 M hydrochloric acid was added and the mixture was again heated at reflux for 1 h. The mixture was cooled to rt and concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoro-N-methylaniline as a light yellow oil (60 mg, 30%). Mass spectrum m/z 204, 206 (M+H)+. the resulting mixture was heated at reflux for 2 h the mixture was again heated at reflux for 1 h concentrated the residue was partitioned between NaHCO3 (aq) and EtOAc The organic phase was washed with brine dried concentrated
Source ID: ord-918542c33672431d8d3b2814f218d362PubChem References
These sources are listed in the compound's public database record.
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