Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | Iodine chloride | HCID 24640 | — |
| Reactant | HCID 90409458 | HCID 90409458 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 90409928 | HCID 90409928 | 99.2% |
Reaction Steps
To a 250-mL round bottom flask, equipped with a stir bar, was added methyl 4-amino-3-chloro-6-(3-fluoro-4-(trimethylsilyl)phenyl)picolinate (0.328 g, 0.930 mmol), and dichloromethane (5.0 mL). To this solution iodine monochloride (0.141 mL, 2.79 mmol) was added. The reaction mixture was allowed to stir at room temperature for 18 hrs. Another portion of iodine monochloride (0.141 mL, 2.79 mmol) was added, and the reaction was allowed to stir at room temperature for an additional 4.5 hrs. The reaction mixture was poured into 1 M Na2SO3, and the layers were partitioned. The aqueous phase was extracted with additional ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound as a white solid (0.375 g, 99%):
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09113629B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-8b338b1521534c59b36654acfdffdd07 |
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| Source note | uspto-grants-2015_08 |
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