Hydrochloric Acid → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1501155Notes

Reaction equation

HRID 1501155 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+].O.Cl>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

Product 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanolYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(5-bromopyridin-2-yl)ethanone (5 g, 25 mmol) in anhydrous ethanol (100 mL) was added sodium borohydride (2.85 g, 75 mmol) at room temperature. After 2 hours, water (10 mL) was added to quench the reaction at 0° C. and then saturated hydrochloric acid aqueous (10 mL) was added the mixture to adjust pH to 7. The mixture was extracted with ethyl acetate (50 mL). The crude product was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to give 1-(5-bromopyridin-2-yl)ethanol (3 g, 60%).

Workup

  1. customto quench
  2. customthe reaction at 0° C.
  3. extractionThe mixture was extracted with ethyl acetate (50 mL)
  4. customThe crude product was purified by column chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-375984d776f04d32bf52301d13a1e24f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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