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

HRID 1365392Notes

Reaction equation

HRID 1365392 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-857142c2cf4d43a4aadb465980be8cb1
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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