HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 5-Fluoropyridine-2-carboxaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Ethyl 5-fluoropyridine-2-carboxylate | HCID 10986675 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Diisobutylaluminum hydride | HCID 14487 | — |
| Product | 5-Fluoropyridine-2-carboxaldehyde | HCID 10351697 | 56.1% |
Reaction Steps
To 5-fluoro-pyridine-2-carboxylic acid ethyl ester (94 mg, 0.556 mmol) in dichloromethane (4.0 mL), 1 M DIBAL in toluene (1.23 mL, 1.23 mmol) was added at room temperature and the mixture was stirred for 30 min. The reaction mixture was quenched with 2 M sodium carbonate and extracted with dichloromethane. The dichloromethane was dried and concentrated to give 39 mg (54.7%) of crude 5-fluoro-pyridine-2-carbaldehyde which could be used for the next step reaction without further purification. GC-MS (M+): 125
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07074809B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-f4e88c7a4f2f4535a5b7fe669b0b17f4 |
| Source note | uspto-grants-2006_07 |