Sodium borohydride → (3-Bromo-5-chloropyridin-4-yl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=[O:9].[BH4-].[Na+]>C1COCC1.O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][OH:9]Participants
6
Procedure
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).
Workup
- washThe organic layer was washed with water and brine
- extractionThe aqueous layer was extracted with DCM
- customThe combined extracts were separated
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2ea079a706e54866b11fb4b926c42829
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519134B2
Reaction notes
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