HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → {2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide | HCID 68603117 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | {2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester | HCID 68602946 | 92.3% |
Reaction Steps
A mixture of 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (442 mg, 1.3 mmol), methylbromoacetate (0.247 mL, 2.6 mmol) and K2CO3 (717 mg, 5.2 mmol) was heated in DMF (8 mL) at 80° C. for 5 hrs. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over Na2SO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) to yield {2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}acetic acid methyl ester (495 mg). MS [M+H]+: 413.9; tR=2.75 min. (method 1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09422310B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-604b4743996f40339109b2643191c2c5 |
| Source note | uspto-grants-2016_08 |