Sodium borohydride → (3-Bromopyridin-2-yl)methanol

HRID 423208Notes

Reaction equation

HRID 423208 reaction equation
C[O:2][C:3]([C:5]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[BH4-].[Na+]>CO>[Br:11][C:10]1[C:5]([CH2:3][OH:2])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

Product 1

HCID 14022521(3-Bromopyridin-2-yl)methanolYield 1,808.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-pyridine-2-carboxylic acid methyl ester (12.8 g, 59 2 mmol) is dissolved in methanol (150 mL) and cooled to 0° C. To the mixture is added NaBH4 (11.2 g, 296 mmol) in 1.0 g portions. The mixture is warmed to room temperature and stirred for 3 h. The methanol is removed under reduced pressure, ethyl acetate is added and the solution is washed with saturated, aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure to yield 6.8 g (62%) of the title compound as a white solid. GCMS m/e 187, 189 [M]−.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. customThe methanol is removed under reduced pressure, ethyl acetate
  3. additionis added
  4. washthe solution is washed with saturated, aqueous ammonium chloride and brine
  5. dry with materialThe organic portion is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29497b18e20f45bebc442b4fded9a82d
Source dataset
uspto-grants-2012_01
Patent number
US08101760B2

Reaction notes

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