Sodium borohydride → (5-Bromopyridin-2-yl)methanol

HRID 881494Notes

Reaction equation

HRID 881494 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

4

Procedure

To a solution of 5-bromopyridine-2-carbaldehyde (300 mg) in methanol (10 mL) was added sodium borohydride (61 mg) and the reaction stirred at room temperature for 72 h. The reaction was quenched with saturated aqueous sodium carbonate solution (20 mL) and water (20 mL) and extracted into dichloromethane (3×30 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give (5-bromo-pyridin-2-yl)-methanol as a white solid.

Workup

  1. customThe reaction was quenched with saturated aqueous sodium carbonate solution (20 mL) and water (20 mL)
  2. extractionextracted into dichloromethane (3×30 mL)
  3. dry with materialThe organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-2837ac9766f6442d9bad4d64a0c97964
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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