Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | HCID 14402958 | HCID 14402958 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 84071066 | HCID 84071066 | 67.3% |
Reaction Steps
Dess-Martin reagent (1.14 g) was added at 0° C. to a methylene chloride (5 mL) solution of (5-bromo-4-methoxypyridin-2-yl)methanol (450 mg) synthesized by the method described in Organic Process Research & Development 2000 4,473. The reaction solution was agitated at 0° C. for 1 hour and further agitated at room temperature for 1 hour. 1N sodium hydroxide solution was added to the reaction solution, the organic layer was separated, and washed with a saturated sodium chloride solution. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 1:1), and 300 mg (67%) 5-bromo-4-methoxypyridine-2-carbaldehyde was obtained. The physical properties of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07880009B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-f7223bbe592f47f59cd72760013664db |
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| Source note | uspto-grants-2011_02 |
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