HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-Fluoro-2-iodo-6-methylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | 2-Bromo-3-fluoro-6-methylpyridine | HCID 24820318 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-Fluoro-2-iodo-6-methylpyridine | HCID 86707391 | 94% |
Reaction Steps
To a solution of 2-bromo-3-fluoro-6-methylpyridine (1000 mg, 5.26 mmol) in 1,4-dioxane (16 mL) were added sodium iodide (1580 mg, 10.52 mmol), copper (I) iodide (150 mg, 0.26 mmol), N,N′-dimethylethylenediamine (62 μL, 0.58 mmol) under argon atmosphere. The reaction solution was heated to reflux for 4 hours, cooled to room temperature, and then to the reaction solution was added water. The mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with aqueous citric acid solution and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 3-fluoro-2-iodo-6-methylpyridine (1169 mg, 94%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987445B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-69cf8ff0eaaa4393939385cc388c468b |
| Source note | uspto-grants-2015_03 |