Sodium borohydride → (5-Bromo-4-chloropyridin-3-yl)methanol

HRID 712750Notes

Reaction equation

HRID 712750 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH:8]=[O:9])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 717423075-Bromo-4-chloropyridine-3-carbaldehyde

Product 1

HCID 117667554(5-Bromo-4-chloropyridin-3-yl)methanolYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-4-chloro-pyridine-3-carbaldehyde (500 mg, 2.27 mmol) is dissolved in MeOH (20 mL) and sodium borohydride (257 mg, 6.80 mmol) is added. The mixture is stirred for 1 hr at room temperature and the solvent is removed in vacuo. Then saturated NH4Cl aqueous solution (20 mL), water (50 mL) and EtOAc (50 mL) are added and the mixture is stirred for 10 min. The aqueous layer is separated and extracted with EtOAc (2×50 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 400 mg of (5-bromo-4-chloro-pyridin-3-yl)-methanol.

Workup

  1. customthe solvent is removed in vacuo
  2. additionThen saturated NH4Cl aqueous solution (20 mL), water (50 mL) and EtOAc (50 mL) are added
  3. stirringthe mixture is stirred for 10 min
  4. customThe aqueous layer is separated
  5. extractionextracted with EtOAc (2×50 mL)
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-8ae8fd23bd394e40a5a101d1d8cd5cdf
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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