3-Acetyl-5-bromopyridine → 3-Bromo-5-(1-hydroxyethyl)pyridine

HRID 712747Notes

Reaction equation

HRID 712747 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8204233-Acetyl-5-bromopyridineHCID 4311764Sodium borohydride

Product 1

HCID 129974353-Bromo-5-(1-hydroxyethyl)pyridineYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(5-Bromo-pyridin-3-yl)-ethanone (3.0 g, 15 mmol) is dissolved in MeOH (20 mL) and sodium borohydride (1.1 g, 30 mmol) is added in 5 small portions every 15 min. The mixture is stirred for 16 hrs and the solvent is then removed in vacuo. Saturated aqueous NH4Cl solution (10 mL) is added along with 30 mL of water. The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 2.9 g of 1-(5-bromo-pyridin-3-yl)-ethanol.

Workup

  1. customthe solvent is then removed in vacuo
  2. additionSaturated aqueous NH4Cl solution (10 mL) is added along with 30 mL of water
  3. extractionThe mixture is extracted with EtOAc (3×50 mL)
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-b255ee28f80d4097bf986fc91a12e407
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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