HCID 86690467, compound → 6-Bromo-5-fluoropicolinaldehyde

HRID 1026741Notes

Reaction equation

HRID 1026741 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[F:10]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[F:10]

Participants

4

Reactant 1

HCID 86690467HCID 86690467, compound

Product 1

HCID 221495566-Bromo-5-fluoropicolinaldehydeYield 40.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Manganese dioxide (695 mg) was added to a solution of (6-bromo-5-fluoropyridin-2-yl)methanol (200 mg) in chloroform (3.00 mL) and the mixture was stirred while heating at 70° C. for 12 hr. After stirring at room temperature for 13 hr, the reaction mixture was filtered through Celite. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-82:18) to afford the title compound (81 mg).

Workup

  1. stirringAfter stirring at room temperature for 13 hr
  2. filtrationthe reaction mixture was filtered through Celite
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-82:18)

Sources & evidence

ORD record
ord-f2f8616fe38a49ccbc691961e332bd84
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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