Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 55139361 | HCID 55139361 | — |
| Reactant | HCID 178418918 | HCID 178418918 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71236679 | HCID 71236679 | 99.5% |
Reaction Steps
To a solution of 5-bromo-2-(3,4-difluorophenoxy)pyridine (19 g, 66.4 mmol) in tetrahydrofuran (THF) (200 mL) was added isopropylmagnesium chloride (66.4 mL, 66.4 mmol). The reaction mixture was stirred at 20° C. for 2 hr, and then I2 (16.86 g, 66.4 mmol) was added, The reaction mixture was stirred at 20° C. for another 4 hr, then saturated aqueous NH4Cl solution (200 ml) and EtOAc (200 ml) were added, the organic layer was separated, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with Hex/EtOAc (20:1). The collected fractions provided 2-(3,4-difluorophenoxy)-5-iodopyridine (22 g, 61.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09273054B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-575a4cb8626443a0990ebaf5226fafbd |
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| Source note | uspto-grants-2016_03 |
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