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

HRID 2367670Notes

Reaction equation

HRID 2367670 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 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromonicotinaldehyde (XXV) (2.05 g, 11.0 mmol) in MeOH (85 mL) was added NaBH4 (832 mg, 21.99 mmol). The reaction was stirred at room temperature for 1 h. The reaction was quenched with saturated aqueous NH4Cl (5 mL) The reaction was concentrated under vacuum and the residue was partitioned between saturated aqueous NH4Cl/EtOAc. The organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated under vacuum to yield crude (5-bromopyridin-3-yl)methanol (XLV) as a golden oil (1.54 g, 8.2 mmol, 74% yield). The product was used without further purification. ESIMS found for C6H6BrNO m/z 188 (M+H).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl (5 mL) The reaction
  2. concentrationwas concentrated under vacuum
  3. customthe residue was partitioned between saturated aqueous NH4Cl/EtOAc
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9484cdd5a02d4887afd7dddad58ee585
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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