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C1=CC(=C(C(=C1C(=O)Cl)F)F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,3,4-trifluorobenzoyl chloride |
|---|---|
| IUPAC Name | — |
| CAS Number | 157373-08-5 |
| Database ID | 2734022 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,3,4-trifluorobenzoyl chloride (CAS 157373-08-5) 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 2734022
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-e2ee5f2468d642c8b47808e42c815c87Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-959ebfdc1c5b4177a805243aa5e4593eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c6ad0708666a4a30a1c39c312089cc74Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The titled compound was prepared according to the procedure of Method D using the product of Example 83D and 2,3,4-trifluorobenzoyl chloride (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.40-7.50 (m, J=9.3, 9.3, 7.0, 2.2 Hz, 1H), 8.10-8.20 (m, 1H), 8.39 (dd, J=5.4, 2.4 Hz, 1H), 9.46 (dd, J=5.3, 1.2 Hz, 1H), 9.87 (dd, J=2.2, 1.2 Hz, 1H) ppm; MS (DCI/NH3) m/z=279 (M+H)+.
Source ID: ord-2265781e88944f8dac266cc7966538e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2,3,4-Trifluorobenzoyl chloride (2.32 mL, 18.16 mmol) was added slowly to a stirred mixture of (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)methylamine (3.44 g, 18.16 mmol) in DCM (200 mL) and 10% aqueous sodium hydroxide solution (200 mL) at 0° C. The reaction was allowed to warm to RT and stirred for a further 24 hours. The phases were separated and the aqueous phase further extracted with DCM (3×100 mL), the combined organics dried (MgSO4), filtered and the solvent removed in vacuo to give a pale yellow oil. The residue was chromatographed on silica, eluting with 0-50% ethyl acetate in isohexane, to give the desired compound as a colourless oil (5.22 g). The phases were separated the aqueous phase further extracted with DCM (3×100 mL) the combined organics dried (MgSO4) filtered the solvent removed in vacuo to give a pale yellow oil The residue was chromatographed on silica eluting with 0-50% ethyl acetate in isohexane
Source ID: ord-5a58a21ddba2451fa62ea92ba1d304c8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2,3,4-Trifluorobenzoylchloride (195 mg, 1 mmol) in DCM (1 mL) was added to a stirred solution of N-benzylaminoethanol (166 mg, 1.1 mmol) in a mixture of DCM (1 mL) and 10% sodium hydroxide solution (1 mL) at 0° C. After the addition of the acid chloride was complete, the mixture was warmed to RT and stirred for approximately 4 hours. The two layers were separated and the aqueous layer was extracted with DCM (3×30 mL). The organic layers were combined, dried (MgSO4), filtered and evaporated to give a colourless oil (190 mg). 1H NMR δ (CDCl3): 3.74 (t, 2H), 3.82 (t, 2H), 4.5 (s, 2H), 4.85 (s, 1H), 7.06 (td, 1H), 7.15 (m, 1H), 7.28-7.37 (m, 1H). m/z 310 (M+H)+ The two layers were separated the aqueous layer was extracted with DCM (3×30 mL) dried (MgSO4) filtered evaporated
Source ID: ord-e0651f92c9204a05a36579039c61cb44Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2,3,4-Trifluorobenzoylchloride (195 mg, 1 mmol) in DCM (1 mL) was added to a stirred solution of N-benzylaminoethanol (166 mg, 1.1 mmol) in a mixture of DCM (1 mL) and 10% sodium hydroxide solution (1 mL) at 0° C. After the addition of the acid chloride was complete, the mixture was warmed to RT and stirred for approximately 4 hours. The two layers were separated and the aqueous layer was extracted with DCM (3×30 mL). The organic layers were combined, dried (MgSO4), filtered and evaporated to give a colourless oil (190 mg). 1H NMR δ (CDCl3): 3.74 (t, 2H), 3.82 (t, 2H), 4.5 (s, 2H), 4.85 (s, 1H), 7.06 (td, 1H), 7.15 (m, 1H), 7.28-7.37 (m, 1H). m/z 310 (M+H)+ The two layers were separated the aqueous layer was extracted with DCM (3×30 mL) dried (MgSO4) filtered evaporated
Source ID: ord-e0651f92c9204a05a36579039c61cb44Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: DIPEA (0.68 mL, 3.9 mmol) was added to a solution of 2,3,4-trifluorobenzoyl chloride (500 mg, 2.6 mmol) in DCM (5 mL) followed by the addition of N-methylethanolamine (0.31 mL, 3.9 mmol). The mixture was stirred for 20 hours. The solution was diluted with methanol (10 mL) and passed through an ISOLUTE® SCX-2 SPE column. The solution was evaporated. The residue was dissolved in DMF and sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) was added portionwise over 5 minutes. The resulting mixture was stirred for 20 hours. Water (100 mL) was added dropwise and the mixture was extracted with ether (3×200 mL). Combined ethereal extracts were dried (MgSO4) and evaporated. The residue was purified by column chromatography (eluting with 1:1 ethyl acetate:isohexane to neat ethyl acetate) to afford the title compound (117 mg, 20%) as a colourless solid. The solution was evaporated The residue was dissolved in DMF The resulting mixture was stirred for 20 hours the mixture was extracted with ether (3×200 mL) were dried (MgSO4) evaporated The residue was purified by column chromatography (eluting with 1:1 ethyl acetate:isohexane to neat ethyl acetate)
Source ID: ord-b45d8d43704e422eb09e2c1f9e231196Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: DIPEA (0.68 mL, 3.9 mmol) was added to a solution of 2,3,4-trifluorobenzoyl chloride (500 mg, 2.6 mmol) in DCM (5 mL) followed by the addition of N-methylethanolamine (0.31 mL, 3.9 mmol). The mixture was stirred for 20 hours. The solution was diluted with methanol (10 mL) and passed through an ISOLUTE® SCX-2 SPE column. The solution was evaporated. The residue was dissolved in DMF and sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) was added portionwise over 5 minutes. The resulting mixture was stirred for 20 hours. Water (100 mL) was added dropwise and the mixture was extracted with ether (3×200 mL). Combined ethereal extracts were dried (MgSO4) and evaporated. The residue was purified by column chromatography (eluting with 1:1 ethyl acetate:isohexane to neat ethyl acetate) to afford the title compound (117 mg, 20%) as a colourless solid. The solution was evaporated The residue was dissolved in DMF The resulting mixture was stirred for 20 hours the mixture was extracted with ether (3×200 mL) were dried (MgSO4) evaporated The residue was purified by column chromatography (eluting with 1:1 ethyl acetate:isohexane to neat ethyl acetate)
Source ID: ord-b45d8d43704e422eb09e2c1f9e231196Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The titled compound was prepared according to the procedure of Method D using the product of Example 83D and 2,3,4-trifluorobenzoyl chloride (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.40-7.50 (m, J=9.3, 9.3, 7.0, 2.2 Hz, 1 H), 8.10-8.20 (m, 1 H), 8.39 (dd, J=5.4, 2.4 Hz, 1 H), 9.46 (dd, J=5.3, 1.2 Hz, 1 H), 9.87 (dd, J=2.2, 1.2 Hz, 1 H) ppm; MS (DCI/NH3) m/z=279 (M+H)+.
Source ID: ord-bc0e7bb9e8604021b4b12e0edd31f82aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e2ee5f2468d642c8b47808e42c815c87Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-959ebfdc1c5b4177a805243aa5e4593ePubChem References
These sources are listed in the compound's public database record.
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