Triacetoxyperiodinane → 5-Bromo-2-chloropyridine-3-carbaldehyde

HRID 515806Notes

Reaction equation

HRID 515806 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[C:5]([Cl:8])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23091039(5-Bromo-2-chloropyridin-3-yl)methanol

Product 1

HCID 230909885-Bromo-2-chloropyridine-3-carbaldehydeYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-2-chloropyridin-3-yl)methanol (6.8 g, 30.6 mmol) in DCM (200 mL), was added Dess-Martin periodinane (32.4 g, 76.6 mmol) at 0° C. The resulting mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (0 to 30% EtOAc in petroleum ether) to afford 5.05 g of 5-bromo-2-chloronicotinaldehyde. LCMS [M+H]+ 221.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (0 to 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-732957e950934f0ba4b72d11177a6eb6
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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