No renderable structure data available
CC(C)(C)NC(=O)C1=C(C=C(C=C1)Br)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromo-N-tert-butyl-2-fluorobenzamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 303084-21-1 |
| Database ID | 22336252 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromo-N-tert-butyl-2-fluorobenzamide (CAS 303084-21-1) 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 22336252
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-a3795c57e9f543ffa141ead6d5133e4dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-N-tert-butyl-2-fluoro-benzamide (1.0 g, 3.65 mmol) and copper(I) cyanide (0.7 g, 7.29 mmol) in anhydrous DMF (10 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and treat with 50% (v/v) aqueous ethylenediamine (20 mL). Extract the reaction mixture with diethyl ether (3×10 mL), combine the organic extracts, wash with brine (2×10 mL) and dry the organic layer over Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2) to obtain the desired intermediate as a white solid (0.6 g, 77%). MS (ES+) m/z: 221 (M+H)+. Extract the reaction mixture with diethyl ether (3×10 mL) wash with brine (2×10 mL) dry the organic layer over Na2SO4 Evaporate the solvent purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2)
Source ID: ord-4a2103c3bf1b4d0ca95aadfb3e1a74c9Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-2-fluoro-benzoic acid (5.0 g, 22.83 mmol), thionyl chloride (10 mL, 0.137 mmol) in toluene (10 mL) and reflux for 2 h. Evaporate the reaction mixture to obtain 4-bromo-2-fluoro-benzoyl chloride (5.0 g, 93%) and use for the next step without further purification. Dissolve tert-butylamine (0.8 mL, 5.12 mmol) and triethylamine (0.8 mL, 6.32 mmol) in anhydrous DCM (20 mL), cool to 0° C. and add a solution of 4-bromo-2-fluoro-benzoyl chloride (1.0 g, 4.22 mmol) in anhydrous DCM (10 mL). Stir the reaction mixture at 0° C. for 10 min, warm to ambient temperature and continue to stir for 30 min. Wash the reaction mixture with brine (2×10 mL), dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (1.0 g, 87%). MS (ES+) m/z: 275 (M+H)+. use for the next step without further purification warm to ambient temperature to stir for 30 min Wash the reaction mixture with brine (2×10 mL) dry the organic extracts over anhydrous Na2SO4 evaporate the solvent purify by chromatography on silica gel eluting with DCM
Source ID: ord-ba2a1e31eb2d4220b16e5fb8a4de677fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-2-fluoro-benzoic acid (5.0 g, 22.83 mmol), thionyl chloride (10 mL, 0.137 mmol) in toluene (10 mL) and reflux for 2 h. Evaporate the reaction mixture to obtain 4-bromo-2-fluoro-benzoyl chloride (5.0 g, 93%) and use for the next step without further purification. Dissolve tert-butylamine (0.8 mL, 5.12 mmol) and triethylamine (0.8 mL, 6.32 mmol) in anhydrous DCM (20 mL), cool to 0° C. and add a solution of 4-bromo-2-fluoro-benzoyl chloride (1.0 g, 4.22 mmol) in anhydrous DCM (10 mL). Stir the reaction mixture at 0° C. for 10 min, warm to ambient temperature and continue to stir for 30 min. Wash the reaction mixture with brine (2×10 mL), dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (1.0 g, 87%). MS (ES+) m/z: 275 (M+H)+. use for the next step without further purification warm to ambient temperature to stir for 30 min Wash the reaction mixture with brine (2×10 mL) dry the organic extracts over anhydrous Na2SO4 evaporate the solvent purify by chromatography on silica gel eluting with DCM
Source ID: ord-ba2a1e31eb2d4220b16e5fb8a4de677fConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound, made in accordance with General Method 3, may be used to prepare compound 3 in accordance with General Method 1. N-tert-Butyl-4-bromo-2-fluorobenzamide (850 mg, 3.1 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.2 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 mL) and water (2 mL) and stirred at RT for 5 min. 2-Acetylcyclohexanone (100 mg, 0.7 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid. extracted with ethyl acetate (50 mL, 2 times) The combined organic layer was dried over Na2SO4 concentrated
Source ID: ord-0cfd027c2a1f49dbb5b991dae66d4545Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared according to General Method 7. N-tert-butyl-4-bromo-2-fluorobenzamide (850 mg, 3.1 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.2 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 ml) and water (2 ml) and stirred at RT for 5 min. 2-acetylcyclohexanone (100 mg, 0.7 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid. The title compound was prepared extracted with ethyl acetate (50 mL, 2 times) The combined organic layer was dried over Na2SO4 concentrated
Source ID: ord-eccd69e3ca9f4232aba44f6cc84e6489Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound, made in accordance with General Method 3, may be used to prepare compound 3 in accordance with General Method 1. N-tert-Butyl-4-bromo-2-fluorobenzamide (850 mg, 3.1 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.2 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 mL) and water (2 mL) and stirred at RT for 5 min. 2-Acetylcyclohexanone (100 mg, 0.7 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid. extracted with ethyl acetate (50 mL, 2 times) The combined organic layer was dried over Na2SO4 concentrated
Source ID: ord-d16c8f1e38ce4c4aa35e2c5c22683e2cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-N-tert-butyl-2-fluoro-benzamide (1.0 g, 3.65 mmol) and copper(I) cyanide (0.7 g, 7.29 mmol) in anhydrous DMF (10 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and treat with 50% (v/v) aqueous ethylenediamine (20 mL). Extract the reaction mixture with diethyl ether (3×10 mL), combine the organic extracts, wash with brine (2×10 mL) and dry the organic layer over Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2) to obtain the desired intermediate as a white solid (0.6 g, 77%). MS (ES+) m/z: 221 (M+H)+. Extract the reaction mixture with diethyl ether (3×10 mL) wash with brine (2×10 mL) dry the organic layer over Na2SO4 Evaporate the solvent purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2)
Source ID: ord-fc1d08ba683a41f19f995569852cc2d2Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-2-fluoro-benzoic acid (5.0 g, 22.83 mmol), thionyl chloride (10 mL, 0.137 mol) in toluene (10 mL) and reflux for 2 h. Evaporate the reaction mixture to obtain 4-bromo-2-fluoro-benzoyl chloride (5.0 g, 93%) and use for the next step without further purification. Dissolve tert-butylamine (0.8 mL, 5.12 mmol) and triethylamine (0.8 mL, 6.32 mmol) in anhydrous DCM (20 mL), cool to 0° C. and add a solution of 4-bromo-2-fluoro-benzoyl chloride (1.0 g, 4.22 mmol) in anhydrous DCM (10 mL). Stir the reaction mixture at 0° C. for 10 min, warm to ambient temperature and continue to stir for 30 min. Wash the reaction mixture with brine (2×10 mL), dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (1.0 g, 87%). MS (ES+) m/z: 275 (M+H)+. use for the next step without further purification warm to ambient temperature to stir for 30 min Wash the reaction mixture with brine (2×10 mL) dry the organic extracts over anhydrous Na2SO4 evaporate the solvent purify by chromatography on silica gel eluting with DCM
Source ID: ord-8066b1f9de3b4fbf9b0e014b64095946Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-N-tert-butyl-2-fluoro-benzamide (1.0 g, 3.65 mmol) and copper(I) cyanide (0.7 g, 7.29 mmol) in anhydrous DMF (10 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and treat with 50% (v/v) aqueous ethylenediamine (20 mL). Extract the reaction mixture with diethyl ether (3×10 mL), combine the organic extracts, wash with brine (2×10 mL) and dry the organic layer over Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2) to obtain the desired intermediate as a white solid (0.6 g, 77%). MS (ES+) m/z: 221 (M+H)+. Extract the reaction mixture with diethyl ether (3×10 mL) wash with brine (2×10 mL) dry the organic layer over Na2SO4 Evaporate the solvent purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1, 7:3 and 3:2)
Source ID: ord-4a2103c3bf1b4d0ca95aadfb3e1a74c9Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-bromo-2-fluoro-benzoic acid (5.0 g, 22.83 mmol), thionyl chloride (10 mL, 0.137 mmol) in toluene (10 mL) and reflux for 2 h. Evaporate the reaction mixture to obtain 4-bromo-2-fluoro-benzoyl chloride (5.0 g, 93%) and use for the next step without further purification. Dissolve tert-butylamine (0.8 mL, 5.12 mmol) and triethylamine (0.8 mL, 6.32 mmol) in anhydrous DCM (20 mL), cool to 0° C. and add a solution of 4-bromo-2-fluoro-benzoyl chloride (1.0 g, 4.22 mmol) in anhydrous DCM (10 mL). Stir the reaction mixture at 0° C. for 10 min, warm to ambient temperature and continue to stir for 30 min. Wash the reaction mixture with brine (2×10 mL), dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (1.0 g, 87%). MS (ES+) m/z: 275 (M+H)+. use for the next step without further purification warm to ambient temperature to stir for 30 min Wash the reaction mixture with brine (2×10 mL) dry the organic extracts over anhydrous Na2SO4 evaporate the solvent purify by chromatography on silica gel eluting with DCM
Source ID: ord-ba2a1e31eb2d4220b16e5fb8a4de677fConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound, made in accordance with General Method 3, may be used to prepare compound 3 in accordance with General Method 1. N-tert-Butyl-4-bromo-2-fluorobenzamide (850 mg, 3.1 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.2 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 mL) and water (2 mL) and stirred at RT for 5 min. 2-Acetylcyclohexanone (100 mg, 0.7 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid. extracted with ethyl acetate (50 mL, 2 times) The combined organic layer was dried over Na2SO4 concentrated
Source ID: ord-0cfd027c2a1f49dbb5b991dae66d4545PubChem References
These sources are listed in the compound's public database record.
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