HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → (3-Bromo-5-chloropyridin-4-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 3-Bromo-5-chloropyridine-4-carboxaldehyde | HCID 73012613 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3-Bromo-5-chloropyridin-4-yl)methanol | HCID 44190471 | 98.7% |
Reaction Steps
To the solution of 3-Bromo-5-chloro-pyridine-4-carbaldehyde (270 mg, 1.23 mmol) in THF (5 mL) and water (1 mL) was added NaBH4 (139 mg, 3.67 mmol). The resulting mixture was stirred for another 1 h, and was diluted with DCM. The organic layer was washed with water and brine. The aqueous layer was extracted with DCM. The combined extracts were separated and concentrated in vacuo to give 270 mg of title compound without further purification. ESI-MS m/z: 223.9 [M+1]+, Retention time 1.01 min. 1H-NMR (CDCl3, 400 MHz) δ 4.88 (s, 2H), 8.46 (s, 1H), 8.56 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519134B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-2ea079a706e54866b11fb4b926c42829 |
| Source note | uspto-grants-2013_08 |