Ammonium Chloride → 6-Bromo-3-pyridinemethanol

HRID 1672861Notes

Reaction equation

HRID 1672861 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[CH:6][N:7]=1

Participants

5

Conditions

Temperature
0 °C

Procedure

6-Bromo-3-pyridinecarboxaldehyde (1.05 g, 5.64 mmol) was dissolved in ethanol (30 mL). The mixture was cooled to 0° C., and stirred at 0° C. for 10 minutes after adding sodium borohydride (213 mg, 5.64 mmol). A saturated aqueous ammonium chloride solution was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (2-bromopyridin-5-yl)methanol (874 mg, 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b09b0e7c7ba48c7809e999a451dcd64
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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