HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Trifluoromethyl)aniline → 3-Bromo-3'-(trifluoromethyl)benzanilide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Trifluoromethyl)aniline | HCID 7375 | — |
| Reactant | 3-Bromobenzoic acid | HCID 11456 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Bromo-3'-(trifluoromethyl)benzanilide | HCID 763883 | — |
Reaction Steps
A mixture of 3-bromobenzoic acid (500 mg, 2.49 mmol), 3-(trifluoromethyl)aniline (0.31 ml, 2.49 mmol) and DIEA (2.06 ml, 12.45 mmol) in DMF (6 ml) was treated with HATU (1.04 g, 2.74 mmol) and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic phase was washed with sat'd NaCl(aq.), dried (MgSO4), filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc) gave a yellow oil which solidified on standing (622 mg, 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889870B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-f0229e9065954d809fbbb90eaac99af9 |
| Source note | uspto-grants-2014_11 |