5-Bromo-3-pyridinecarboxaldehyde → (5-Bromo-3-pyridinyl)methanol

HRID 877123Notes

Reaction equation

HRID 877123 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromonicotinaldehyde (XLV) (2.0 g, 10.8 mmol, 1 eq) in MeOH (20 mL) was added NaBH4 (2.4 g, 64.9 mmol, 6 eq) and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was diluted in water (15 mL), the aqueous phase was extracted with DCM (10 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford (5-bromopyridin-3-yl)methanol (LII) (1.8 g, 9.57 mmol, 90.0% yield) as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ ppm 4.73 (s, 2H), 7.90 (s, 1H), 8.47 (s, 1H), 8.57 (s, 1H). ESIMS found for C6H6BrNO m/z 188 (M+H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted in water (15 mL)
  3. extractionthe aqueous phase was extracted with DCM (10 mL×3)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a40832a344c4c2a8b97c53ce7110f7a
Source dataset
uspto-grants-2015_03
Patent number
US08987298B2

Reaction notes

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