No renderable structure data available
C1=CC=C(C=C1)CC(=O)NC2=CC(=CC=C2)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-(3-bromophenyl)-2-phenylacetamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 13140-73-3 |
| Database ID | 710468 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-(3-bromophenyl)-2-phenylacetamide (CAS 13140-73-3) 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 710468
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5d13194241804fd0af961fc6d013a9dcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-13c315ee9af048a3838c71e7469f0d60Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of crude N-(3-bromophenyl)-2-phenylacetamide (3.02 g, 10.4 mmol) in dry tetrahydrofuran (25 mL) was added 1.0 N borane-tetrahydrofuran complex (1:1. 26 mL, 26.12 mmol) from an addition funnel at 0° C. The reaction was refluxed under nitrogen overnight. Reaction mixture was cooled to room temperature, treated with 2.0 N aqueous sodium hydroxide (30 mL) and then stirred for 20 min. The reaction was then cooled again at 0° C. and neutralized with 2.0 N aqueous hydrochloric acid (60 mL) and further stirred for 30 min. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford 3-Bromo-N-(2-phenylethyl)aniline (2.55 g, 85% yield) as brown oil with reasonable purity: 1H NMR (400 MHz, CDCl3): 7.30 (t, 2H), 7.20 (m, 3H), 6.95 (t, 1H), 6.78 (br d, 1H), 6.70 (t, 1H), 6.45 (dd, 1H), 3.62 (br s, 1H), 3.40 (m, 2H), 2.92 (t, 2H); MS (EI) for C14H12NOBr: 290 MH+). The reaction was refluxed under nitrogen overnight Reaction mixture further stirred for 30 min The aqueous layer was extracted with ethyl acetate (3×100 mL) The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL) dried over magnesium sulfate filtered concentrated
Source ID: ord-80fd6c348f1745e8b81a184ad50a21f5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of crude N-(3-bromophenyl)-2-phenylacetamide (3.02 g, 10.4 mmol) in dry tetrahydrofuran (25 mL) was added 1.0 N borane-tetrahydrofuran complex (1:1. 26 mL, 26.12 mmol) from an addition funnel at 0° C. The reaction was refluxed under nitrogen overnight. Reaction mixture was cooled to room temperature, treated with 2.0 N aqueous sodium hydroxide (30 mL) and then stirred for 20 min. The reaction was then cooled again at 0° C. and neutralized with 2.0 N aqueous hydrochloric acid (60 mL) and further stirred for 30 min. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford 3-Bromo-N-(2-phenylethyl)aniline (2.55 g, 85% yield) as brown oil with reasonable purity: 1H NMR (400 MHz, CDCl3): 7.30 (t, 2H), 7.20 (m, 3H), 6.95 (t, 1H), 6.78 (br d, 1H), 6.70 (t, 1H), 6.45 (dd, 1H), 3.62 (br s, 1H), 3.40 (m, 2H), 2.92 (t, 2H); MS (EI) for C14H12NOBr: 290 MH+). The reaction was refluxed under nitrogen overnight Reaction mixture further stirred for 30 min The aqueous layer was extracted with ethyl acetate (3×100 mL) The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL) dried over magnesium sulfate filtered concentrated
Source ID: ord-80fd6c348f1745e8b81a184ad50a21f5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromoaniline (3.21 g, 18.60 mmol) in dry tetrahydrofuran (45 mL) were added triethylamine (2.82 g, 27.91 mmol) and phenylacetyl chloride 93.45 g, 22.30 mmol) at 0° C. The reaction warmed to room temperature and stirred for 4 h. The reaction mixture was treated with 2.0 N aqueous hydrochloric acid (20 mL) at 0° C. and diluted with ethyl acetate (300 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude N-(3-bromophenyl)-2-phenylacetamide (4.84 g, 86% yield) which was used in the next step without any further purification. The organic layer was washed with water (20 mL), saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL) dried over magnesium sulfate filtered concentrated
Source ID: ord-e94d7cba80654bad807437637dd9cee7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-13c315ee9af048a3838c71e7469f0d60Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of crude N-(3-bromophenyl)-2-phenylacetamide (3.02 g, 10.4 mmol) in dry tetrahydrofuran (25 mL) was added 1.0 N borane-tetrahydrofuran complex (1:1. 26 mL, 26.12 mmol) from an addition funnel at 0° C. The reaction was refluxed under nitrogen overnight. Reaction mixture was cooled to room temperature, treated with 2.0 N aqueous sodium hydroxide (30 mL) and then stirred for 20 min. The reaction was then cooled again at 0° C. and neutralized with 2.0 N aqueous hydrochloric acid (60 mL) and further stirred for 30 min. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford 3-Bromo-N-(2-phenylethyl)aniline (2.55 g, 85% yield) as brown oil with reasonable purity: 1H NMR (400 MHz, CDCl3): 7.30 (t, 2H), 7.20 (m, 3H), 6.95 (t, 1H), 6.78 (br d, 1H), 6.70 (t, 1H), 6.45 (dd, 1H), 3.62 (br s, 1H), 3.40 (m, 2H), 2.92 (t, 2H); MS (EI) for C14H12NOBr: 290 MH+). The reaction was refluxed under nitrogen overnight Reaction mixture further stirred for 30 min The aqueous layer was extracted with ethyl acetate (3×100 mL) The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL) dried over magnesium sulfate filtered concentrated
Source ID: ord-80fd6c348f1745e8b81a184ad50a21f5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromoaniline (3.21 g, 18.60 mmol) in dry tetrahydrofuran (45 mL) were added triethylamine (2.82 g, 27.91 mmol) and phenylacetyl chloride 93.45 g, 22.30 mmol) at 0° C. The reaction warmed to room temperature and stirred for 4 h. The reaction mixture was treated with 2.0 N aqueous hydrochloric acid (20 mL) at 0° C. and diluted with ethyl acetate (300 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford crude N-(3-bromophenyl)-2-phenylacetamide (4.84 g, 86% yield) which was used in the next step without any further purification. The organic layer was washed with water (20 mL), saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL) dried over magnesium sulfate filtered concentrated
Source ID: ord-e94d7cba80654bad807437637dd9cee7PubChem References
These sources are listed in the compound's public database record.
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