HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-Bromo-2-(2,4-dichlorophenylamino)-3,4-difluorobenzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | 5-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester | HCID 86596771 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-Bromo-2-(2,4-dichlorophenylamino)-3,4-difluorobenzoic acid methyl ester | HCID 86598634 | 89.4% |
Reaction Steps
A mixture of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.07 g, 5.50 mmol), NCS (789 mg, 5.91 mmol), and catalytic amount of conc. HCl in DMF (41 mL) was stirred for 1 hour at room temperature. The reaction mixture was diluted with EtOAc, and washed with water (5×). The organic layer was dried over MgSO4, filtered, and concentrated to give the crude material which was purified by silica gel flash column chromatography (3 to 5% EtOAc in hexanes) to afford the desired product (2.02 g, 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07772234B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-ad98965cdfdb47918d349fa4da4c0ab2 |
| Source note | uspto-grants-2010_08 |