HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Methyl 2-amino-5-bromo-3-methoxybenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Methyl 2-amino-3-methoxybenzoate | HCID 602320 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 2-amino-5-bromo-3-methoxybenzoate | HCID 13894022 | 86% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
To a solution of compound 53 (22.4 g, 123 mmol) in DMF (250 mL) was added N-bromosuccinimide (21.9 g, 123 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 0.5 h. To the mixture was added water and extracted with EtOAc (500 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired compound 54 (27.5 g, 86%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09034921B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-dd0c574c13a842c8a23be71b3f6275b0 |
| Source note | uspto-grants-2015_05 |