Triacetoxyperiodinane → 3-Bromo-4-methylpyridine-2-carbaldehyde

HRID 468943Notes

Reaction equation

HRID 468943 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23344241(3-Bromo-4-methylpyridin-2-yl)methanol

Product 1

HCID 866749793-Bromo-4-methylpyridine-2-carbaldehydeYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (3-bromo-4-methyl-2-pyridyl)methanol (600 mg, 2.97 mmol) and Dess-Martin Periodinane (1688 mg, 3.86 mmol) in DCM (20 mL) was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (2×25 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (12 g, Silica, 0-80% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as pale yellow solid (470 mg, 79%), which was used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (2×25 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by flash chromatography (12 g, Silica, 0-80% ethyl acetate in heptane)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-56232b55c8b9427baa6d92938612315f
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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